# Electronic Supplementary Material (ESI) for RSC Medicinal 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_5a_pani123_mecn
_database_code_depnum_ccdc_archive 'CCDC 2331158'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
3-methoxy-6,6-dimethyl-2-(4-nitrophenyl)-3,5,6,7-tetrahydro-4H-benzo[d]imidazol-4-one
_chemical_formula_moiety         'C16 H17 N3 O4'
_chemical_formula_sum            'C16 H17 N3 O4'
_chemical_formula_weight         315.32
_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'

_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                   8.7742(9)
_cell_length_b                   9.1629(9)
_cell_length_c                   10.6026(10)
_cell_angle_alpha                86.044(8)
_cell_angle_beta                 88.978(8)
_cell_angle_gamma                65.694(9)
_cell_volume                     774.96(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3437
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9160
_cell_measurement_theta_min      2.6960
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60728
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.808
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8302
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_min         2.547
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.808
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00  240.00    --    0.00   0.00  45.00  180
  2  ω    -30.00  90.00   1.00  240.00    --    0.00  72.00  70.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω 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                2492
_reflns_number_total             3097
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.046
_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)+(0.0567P)²+0.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1137
_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 Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C5A(H5AA), C3A(H3A), C2A(H2A)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_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 0.57814(13) 0.10473(11) 0.60255(9) 0.0588(3) Uani 1 1 d . . . . .
N1 N 0.53297(14) 0.20847(13) 0.49518(10) 0.0488(3) Uani 1 1 d . . . . .
N3 N 0.39153(14) 0.41765(13) 0.36444(10) 0.0488(3) Uani 1 1 d . . . . .
O2 O 0.86232(15) -0.05805(14) 0.42392(11) 0.0770(4) Uani 1 1 d . . . . .
O3 O -0.15474(17) 0.54942(18) 0.91274(13) 0.0891(4) Uani 1 1 d . . . . .
N2 N -0.12377(17) 0.63324(19) 0.83165(13) 0.0656(4) Uani 1 1 d . . . . .
C4 C 0.53233(17) 0.31835(15) 0.30714(12) 0.0459(3) Uani 1 1 d . . . . .
C2 C 0.39386(17) 0.34812(15) 0.48027(13) 0.0463(3) Uani 1 1 d . . . . .
O4 O -0.1954(2) 0.77810(18) 0.82324(16) 0.1079(6) Uani 1 1 d . . . . .
C6 C 0.70287(17) 0.18388(17) 0.12384(13) 0.0512(3) Uani 1 1 d . . . . .
C1A C 0.26313(17) 0.41627(15) 0.57392(13) 0.0464(3) Uani 1 1 d . . . . .
C9 C 0.62427(17) 0.18665(16) 0.38571(13) 0.0476(3) Uani 1 1 d . . . . .
C5 C 0.58596(19) 0.34412(16) 0.17672(13) 0.0525(3) Uani 1 1 d . . . . .
H5A H 0.643593 0.414496 0.177481 0.063 Uiso 1 1 calc R U . . .
H5B H 0.488199 0.396062 0.122131 0.063 Uiso 1 1 calc R U . . .
C4A C 0.00807(18) 0.55676(18) 0.74058(14) 0.0526(3) Uani 1 1 d . . . . .
C6A C 0.14296(17) 0.57237(16) 0.54774(13) 0.0488(3) Uani 1 1 d . . . . .
H6A H 0.149135 0.628934 0.472968 0.059 Uiso 1 1 calc R U . . .
C8 C 0.78073(18) 0.05796(16) 0.35357(14) 0.0515(3) Uani 1 1 d . . . . .
C7 C 0.83877(18) 0.08415(17) 0.22250(14) 0.0543(4) Uani 1 1 d . . . . .
H7A H 0.902731 -0.020166 0.190402 0.065 Uiso 1 1 calc R U . . .
H7B H 0.914409 0.136202 0.229580 0.065 Uiso 1 1 calc R U . . .
C5A C 0.01577(18) 0.64390(17) 0.63048(14) 0.0512(3) Uani 1 1 d . . . . .
H5AA H -0.063271 0.748342 0.612975 0.061 Uiso 1 1 calc R U . . .
C3A C 0.1221(2) 0.40173(19) 0.76839(15) 0.0622(4) Uani 1 1 d . . . . .
H3A H 0.113161 0.344960 0.842237 0.075 Uiso 1 1 calc R U . . .
C2A C 0.2495(2) 0.33194(18) 0.68536(15) 0.0601(4) Uani 1 1 d . . . . .
H2A H 0.327659 0.227275 0.703552 0.072 Uiso 1 1 calc R U . . .
C11 C 0.6030(2) 0.0893(2) 0.09015(17) 0.0692(5) Uani 1 1 d . . . . .
H11A H 0.547890 0.069455 0.164118 0.104 Uiso 1 1 calc R U . . .
H11B H 0.677282 -0.011087 0.058866 0.104 Uiso 1 1 calc R U . . .
H11C H 0.521092 0.149995 0.026238 0.104 Uiso 1 1 calc R U . . .
C10 C 0.7875(2) 0.2189(2) 0.00545(16) 0.0738(5) Uani 1 1 d . . . . .
H10A H 0.703720 0.286961 -0.054792 0.111 Uiso 1 1 calc R U . . .
H10B H 0.855345 0.119977 -0.031009 0.111 Uiso 1 1 calc R U . . .
H10C H 0.856592 0.271827 0.027818 0.111 Uiso 1 1 calc R U . . .
C12 C 0.6968(2) 0.1367(2) 0.67627(16) 0.0758(5) Uani 1 1 d . . . . .
H12A H 0.798036 0.112264 0.629425 0.114 Uiso 1 1 calc R U . . .
H12B H 0.721059 0.071225 0.754247 0.114 Uiso 1 1 calc R U . . .
H12C H 0.650073 0.247913 0.694073 0.114 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
O1 N1 1.3832(14) . ?
O1 C12 1.4467(19) . ?
N1 C2 1.3585(17) . ?
N1 C9 1.3769(18) . ?
N3 C4 1.3592(18) . ?
N3 C2 1.3404(17) . ?
O2 C8 1.2173(17) . ?
O3 N2 1.2145(18) . ?
N2 O4 1.2099(19) . ?
N2 C4A 1.466(2) . ?
C4 C9 1.3729(18) . ?
C4 C5 1.487(2) . ?
C2 C1A 1.465(2) . ?
C6 C5 1.541(2) . ?
C6 C7 1.538(2) . ?
C6 C11 1.525(2) . ?
C6 C10 1.529(2) . ?
C1A C6A 1.396(2) . ?
C1A C2A 1.397(2) . ?
C9 C8 1.448(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4A C5A 1.385(2) . ?
C4A C3A 1.374(2) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.374(2) . ?
C8 C7 1.509(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5A H5AA 0.9300 . ?
C3A H3A 0.9300 . ?
C3A C2A 1.374(2) . ?
C2A H2A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C12 109.34(11) . . ?
C2 N1 O1 126.17(11) . . ?
C2 N1 C9 108.87(11) . . ?
C9 N1 O1 124.96(11) . . ?
C2 N3 C4 105.81(11) . . ?
O3 N2 C4A 118.95(15) . . ?
O4 N2 O3 123.03(16) . . ?
O4 N2 C4A 118.01(14) . . ?
N3 C4 C9 111.39(12) . . ?
N3 C4 C5 126.12(12) . . ?
C9 C4 C5 122.49(13) . . ?
N1 C2 C1A 126.59(12) . . ?
N3 C2 N1 109.74(12) . . ?
N3 C2 C1A 123.67(12) . . ?
C7 C6 C5 109.94(11) . . ?
C11 C6 C5 110.15(12) . . ?
C11 C6 C7 109.58(13) . . ?
C11 C6 C10 109.52(13) . . ?
C10 C6 C5 108.95(12) . . ?
C10 C6 C7 108.68(13) . . ?
C6A C1A C2 117.79(12) . . ?
C6A C1A C2A 118.56(13) . . ?
C2A C1A C2 123.62(13) . . ?
N1 C9 C8 130.50(13) . . ?
C4 C9 N1 104.19(12) . . ?
C4 C9 C8 125.31(13) . . ?
C4 C5 C6 111.16(11) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5A C4A N2 119.02(14) . . ?
C3A C4A N2 118.86(14) . . ?
C3A C4A C5A 122.11(14) . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A C1A 121.16(13) . . ?
C5A C6A H6A 119.4 . . ?
O2 C8 C9 125.04(14) . . ?
O2 C8 C7 122.08(13) . . ?
C9 C8 C7 112.84(12) . . ?
C6 C7 H7A 108.0 . . ?
C6 C7 H7B 108.0 . . ?
C8 C7 C6 117.02(12) . . ?
C8 C7 H7A 108.0 . . ?
C8 C7 H7B 108.0 . . ?
H7A C7 H7B 107.3 . . ?
C4A C5A H5AA 120.8 . . ?
C6A C5A C4A 118.40(13) . . ?
C6A C5A H5AA 120.8 . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A C4A 118.94(14) . . ?
C2A C3A H3A 120.5 . . ?
C1A C2A H2A 119.6 . . ?
C3A C2A C1A 120.82(14) . . ?
C3A C2A H2A 119.6 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 N1 C2 N3 179.56(11) . . . . ?
O1 N1 C2 C1A -0.6(2) . . . . ?
O1 N1 C9 C4 -179.66(11) . . . . ?
O1 N1 C9 C8 0.7(2) . . . . ?
N1 C2 C1A C6A 170.63(13) . . . . ?
N1 C2 C1A C2A -11.5(2) . . . . ?
N1 C9 C8 O2 -0.9(3) . . . . ?
N1 C9 C8 C7 -178.81(13) . . . . ?
N3 C4 C9 N1 0.27(15) . . . . ?
N3 C4 C9 C8 179.94(12) . . . . ?
N3 C4 C5 C6 -155.90(13) . . . . ?
N3 C2 C1A C6A -9.6(2) . . . . ?
N3 C2 C1A C2A 168.33(13) . . . . ?
O2 C8 C7 C6 153.76(15) . . . . ?
O3 N2 C4A C5A 163.66(14) . . . . ?
O3 N2 C4A C3A -17.6(2) . . . . ?
N2 C4A C5A C6A 178.07(12) . . . . ?
N2 C4A C3A C2A -177.56(14) . . . . ?
C4 N3 C2 N1 0.01(15) . . . . ?
C4 N3 C2 C1A -179.82(12) . . . . ?
C4 C9 C8 O2 179.48(15) . . . . ?
C4 C9 C8 C7 1.6(2) . . . . ?
C2 N1 C9 C4 -0.26(15) . . . . ?
C2 N1 C9 C8 -179.90(14) . . . . ?
C2 N3 C4 C9 -0.18(15) . . . . ?
C2 N3 C4 C5 -179.84(13) . . . . ?
C2 C1A C6A C5A 179.46(12) . . . . ?
C2 C1A C2A C3A -178.81(14) . . . . ?
O4 N2 C4A C5A -17.3(2) . . . . ?
O4 N2 C4A C3A 161.44(17) . . . . ?
C1A C6A C5A C4A -0.7(2) . . . . ?
C9 N1 C2 N3 0.16(15) . . . . ?
C9 N1 C2 C1A 179.98(12) . . . . ?
C9 C4 C5 C6 24.48(19) . . . . ?
C9 C8 C7 C6 -28.30(18) . . . . ?
C5 C4 C9 N1 179.94(12) . . . . ?
C5 C4 C9 C8 -0.4(2) . . . . ?
C5 C6 C7 C8 51.83(17) . . . . ?
C4A C3A C2A C1A -0.3(3) . . . . ?
C6A C1A C2A C3A -0.9(2) . . . . ?
C7 C6 C5 C4 -47.31(16) . . . . ?
C5A C4A C3A C2A 1.2(2) . . . . ?
C3A C4A C5A C6A -0.7(2) . . . . ?
C2A C1A C6A C5A 1.5(2) . . . . ?
C11 C6 C5 C4 73.54(15) . . . . ?
C11 C6 C7 C8 -69.37(16) . . . . ?
C10 C6 C5 C4 -166.30(13) . . . . ?
C10 C6 C7 C8 170.99(13) . . . . ?
C12 O1 N1 C2 -97.23(16) . . . . ?
C12 O1 N1 C9 82.08(16) . . . . ?

_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
- Detector area scaling
;
####################################################################### 
# 
# 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_3c_pani152_dmfa
_database_code_depnum_ccdc_archive 'CCDC 2336792'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 F3 N2 O2'
_chemical_formula_sum            'C16 H15 F3 N2 O2'
_chemical_formula_weight         324.30
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8260(13)
_cell_length_b                   25.780(3)
_cell_length_c                   11.897(3)
_cell_angle_alpha                90
_cell_angle_beta                 122.66(3)
_cell_angle_gamma                90
_cell_volume                     1504.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2540
_cell_measurement_theta_min      3.0930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15466
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.192
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       ?
_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                2298
_reflns_number_total             3203
_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 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023) (IMPORT)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0836
_refine_ls_restrained_S_all      1.064
_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)+(0.1501P)²+0.6524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2347
_refine_ls_wR_factor_ref         0.2493
_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. Rigid bond restraints
 F2, F6, F4, F1, F5, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F2 \\sim F6 \\sim F4 \\sim F1 \\sim F5 \\sim F3: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(F1)=Sof(F5)=Sof(F3)=1-FVAR(1)
 Sof(F2)=Sof(F6)=Sof(F4)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C3A(H3A), C2A(H2A), C6A(H6A), C5A(H5AA)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_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
F2 F -0.221(5) 0.5396(8) 0.4311(19) 0.092(5) Uani 0.47(5) 1 d . U P A 1
F6 F -0.508(3) 0.5616(9) 0.231(3) 0.075(4) Uani 0.47(5) 1 d . U P A 1
F4 F -0.182(5) 0.5146(10) 0.264(3) 0.082(4) Uani 0.47(5) 1 d . U P A 1
F1 F -0.277(4) 0.5417(6) 0.4122(19) 0.075(3) Uani 0.53(5) 1 d . U P A 2
F5 F -0.488(4) 0.5565(10) 0.205(3) 0.104(6) Uani 0.53(5) 1 d . U P A 2
F3 F -0.125(4) 0.5090(7) 0.311(2) 0.077(3) Uani 0.53(5) 1 d . U P A 2
O1 O 0.8381(4) 0.70910(8) 0.5856(2) 0.0494(6) Uani 1 1 d . . . . .
N1 N 0.6784(5) 0.74008(9) 0.4824(2) 0.0359(6) Uani 1 1 d . . . . .
N3 N 0.3180(5) 0.77301(9) 0.3073(2) 0.0382(6) Uani 1 1 d . . . . .
H3 H 0.152104 0.777011 0.241736 0.046 Uiso 1 1 calc R U . . .
O2 O 1.2320(5) 0.79115(11) 0.5961(3) 0.0658(8) Uani 1 1 d . . . . .
C4 C 0.5228(6) 0.80639(11) 0.3412(3) 0.0378(7) Uani 1 1 d . . . . .
C1A C 0.2496(5) 0.68671(11) 0.3795(3) 0.0357(6) Uani 1 1 d . . . . .
C2 C 0.4133(6) 0.73206(11) 0.3924(3) 0.0353(6) Uani 1 1 d . . . . .
C9 C 0.7531(6) 0.78685(11) 0.4519(3) 0.0382(7) Uani 1 1 d . . . . .
C4A C -0.0723(6) 0.60034(12) 0.3383(3) 0.0423(7) Uani 1 1 d . . . . .
C3A C 0.2083(6) 0.59564(12) 0.4096(3) 0.0449(7) Uani 1 1 d . . . . .
H3A H 0.289336 0.563512 0.443134 0.054 Uiso 1 1 calc R U . . .
C2A C 0.3686(6) 0.63876(11) 0.4309(3) 0.0412(7) Uani 1 1 d . . . . .
H2A H 0.557444 0.635567 0.480150 0.049 Uiso 1 1 calc R U . . .
C8 C 1.0194(6) 0.80976(12) 0.5065(3) 0.0427(7) Uani 1 1 d . . . . .
C6A C -0.0346(6) 0.69105(11) 0.3076(3) 0.0407(7) Uani 1 1 d . . . . .
H6A H -0.116622 0.723031 0.273038 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5108(7) 0.85474(12) 0.2692(3) 0.0472(8) Uani 1 1 d . . . . .
H5A H 0.340360 0.872659 0.238356 0.057 Uiso 1 1 calc R U . . .
H5B H 0.517922 0.845934 0.191869 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7515(6) 0.89047(12) 0.3626(3) 0.0444(7) Uani 1 1 d . . . . .
C5A C -0.1948(6) 0.64794(12) 0.2875(3) 0.0431(7) Uani 1 1 d . . . . .
H5AA H -0.383620 0.650998 0.240172 0.052 Uiso 1 1 calc R U . . .
C7 C 1.0157(6) 0.85831(13) 0.4329(4) 0.0503(8) Uani 1 1 d . . . . .
H7A H 1.054931 0.848111 0.366504 0.060 Uiso 1 1 calc R U . . .
H7B H 1.163209 0.880670 0.496447 0.060 Uiso 1 1 calc R U . . .
C1 C -0.2424(7) 0.55319(13) 0.3151(4) 0.0540(9) Uani 1 1 d . . . . .
C11 C 0.7776(8) 0.93260(15) 0.2793(4) 0.0632(10) Uani 1 1 d . . . . .
H11A H 0.916764 0.956820 0.337680 0.095 Uiso 1 1 calc R U . . .
H11B H 0.606896 0.950463 0.226596 0.095 Uiso 1 1 calc R U . . .
H11C H 0.825580 0.916914 0.221538 0.095 Uiso 1 1 calc R U . . .
C10 C 0.7062(9) 0.91551(15) 0.4652(4) 0.0653(10) Uani 1 1 d . . . . .
H10A H 0.862565 0.935998 0.526145 0.098 Uiso 1 1 calc R U . . .
H10B H 0.679719 0.888962 0.513776 0.098 Uiso 1 1 calc R U . . .
H10C H 0.547735 0.937326 0.420426 0.098 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
F2 C1 1.363(18) . ?
F6 C1 1.331(19) . ?
F4 C1 1.31(2) . ?
F1 C1 1.308(15) . ?
F5 C1 1.32(2) . ?
F3 C1 1.344(19) . ?
O1 N1 1.333(3) . ?
N1 C2 1.338(4) . ?
N1 C9 1.395(4) . ?
N3 H3 0.8600 . ?
N3 C4 1.344(4) . ?
N3 C2 1.357(4) . ?
O2 C8 1.214(4) . ?
C4 C9 1.372(4) . ?
C4 C5 1.493(4) . ?
C1A C2 1.463(4) . ?
C1A C2A 1.388(4) . ?
C1A C6A 1.399(4) . ?
C9 C8 1.446(4) . ?
C4A C3A 1.382(4) . ?
C4A C5A 1.384(4) . ?
C4A C1 1.497(5) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.385(4) . ?
C2A H2A 0.9300 . ?
C8 C7 1.521(5) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.387(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.539(4) . ?
C6 C7 1.538(4) . ?
C6 C11 1.532(5) . ?
C6 C10 1.525(5) . ?
C5A H5AA 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C2 125.1(2) . . ?
O1 N1 C9 126.6(2) . . ?
C2 N1 C9 108.2(2) . . ?
C4 N3 H3 125.2 . . ?
C4 N3 C2 109.6(2) . . ?
C2 N3 H3 125.2 . . ?
N3 C4 C9 107.6(3) . . ?
N3 C4 C5 127.1(3) . . ?
C9 C4 C5 125.2(3) . . ?
C2A C1A C2 121.6(3) . . ?
C2A C1A C6A 119.0(3) . . ?
C6A C1A C2 119.3(3) . . ?
N1 C2 N3 107.9(3) . . ?
N1 C2 C1A 127.8(3) . . ?
N3 C2 C1A 124.2(2) . . ?
N1 C9 C8 130.3(3) . . ?
C4 C9 N1 106.7(2) . . ?
C4 C9 C8 122.5(3) . . ?
C3A C4A C5A 120.4(3) . . ?
C3A C4A C1 119.2(3) . . ?
C5A C4A C1 120.4(3) . . ?
C4A C3A H3A 120.0 . . ?
C4A C3A C2A 120.0(3) . . ?
C2A C3A H3A 120.0 . . ?
C1A C2A H2A 119.8 . . ?
C3A C2A C1A 120.5(3) . . ?
C3A C2A H2A 119.8 . . ?
O2 C8 C9 124.9(3) . . ?
O2 C8 C7 121.4(3) . . ?
C9 C8 C7 113.5(3) . . ?
C1A C6A H6A 119.8 . . ?
C5A C6A C1A 120.4(3) . . ?
C5A C6A H6A 119.8 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.1(2) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C7 C6 C5 108.9(3) . . ?
C11 C6 C5 109.1(3) . . ?
C11 C6 C7 108.3(3) . . ?
C10 C6 C5 110.3(3) . . ?
C10 C6 C7 110.3(3) . . ?
C10 C6 C11 109.8(3) . . ?
C4A C5A C6A 119.7(3) . . ?
C4A C5A H5AA 120.2 . . ?
C6A C5A H5AA 120.2 . . ?
C8 C7 C6 117.1(3) . . ?
C8 C7 H7A 108.0 . . ?
C8 C7 H7B 108.0 . . ?
C6 C7 H7A 108.0 . . ?
C6 C7 H7B 108.0 . . ?
H7A C7 H7B 107.3 . . ?
F2 C1 C4A 109.4(10) . . ?
F6 C1 F2 103.5(13) . . ?
F6 C1 C4A 113.1(11) . . ?
F4 C1 F2 111.9(15) . . ?
F4 C1 F6 105.9(14) . . ?
F4 C1 C4A 112.7(10) . . ?
F1 C1 F5 107.1(13) . . ?
F1 C1 F3 99.6(11) . . ?
F1 C1 C4A 115.0(8) . . ?
F5 C1 F3 108.4(12) . . ?
F5 C1 C4A 112.5(11) . . ?
F3 C1 C4A 113.4(9) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
_geom_hbond_publ_flag
N3 H3 O1 0.86 1.80 2.651(3) 167.4 4_475 yes

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 N1 C2 N3 176.9(3) . . . . ?
O1 N1 C2 C1A -6.1(5) . . . . ?
O1 N1 C9 C4 -177.5(3) . . . . ?
O1 N1 C9 C8 11.1(5) . . . . ?
N1 C9 C8 O2 -2.5(6) . . . . ?
N1 C9 C8 C7 172.5(3) . . . . ?
N3 C4 C9 N1 0.5(3) . . . . ?
N3 C4 C9 C8 172.6(3) . . . . ?
N3 C4 C5 C6 161.0(3) . . . . ?
O2 C8 C7 C6 -157.1(3) . . . . ?
C4 N3 C2 N1 1.4(3) . . . . ?
C4 N3 C2 C1A -175.8(3) . . . . ?
C4 C9 C8 O2 -172.7(3) . . . . ?
C4 C9 C8 C7 2.4(5) . . . . ?
C4 C5 C6 C7 47.8(4) . . . . ?
C4 C5 C6 C11 165.9(3) . . . . ?
C4 C5 C6 C10 -73.5(4) . . . . ?
C1A C6A C5A C4A -0.4(5) . . . . ?
C2 N1 C9 C4 0.3(3) . . . . ?
C2 N1 C9 C8 -171.0(3) . . . . ?
C2 N3 C4 C9 -1.1(3) . . . . ?
C2 N3 C4 C5 176.0(3) . . . . ?
C2 C1A C2A C3A -175.5(3) . . . . ?
C2 C1A C6A C5A 176.3(3) . . . . ?
C9 N1 C2 N3 -1.0(3) . . . . ?
C9 N1 C2 C1A 176.0(3) . . . . ?
C9 C4 C5 C6 -22.4(5) . . . . ?
C9 C8 C7 C6 27.7(4) . . . . ?
C4A C3A C2A C1A -1.0(5) . . . . ?
C3A C4A C5A C6A 0.5(5) . . . . ?
C3A C4A C1 F2 73.2(11) . . . . ?
C3A C4A C1 F6 -172.0(13) . . . . ?
C3A C4A C1 F4 -52.0(17) . . . . ?
C3A C4A C1 F1 84.7(11) . . . . ?
C3A C4A C1 F5 -152.4(17) . . . . ?
C3A C4A C1 F3 -29.0(12) . . . . ?
C2A C1A C2 N1 -22.5(5) . . . . ?
C2A C1A C2 N3 154.1(3) . . . . ?
C2A C1A C6A C5A -0.4(5) . . . . ?
C6A C1A C2 N1 160.9(3) . . . . ?
C6A C1A C2 N3 -22.5(4) . . . . ?
C6A C1A C2A C3A 1.1(5) . . . . ?
C5 C4 C9 N1 -176.7(3) . . . . ?
C5 C4 C9 C8 -4.5(5) . . . . ?
C5 C6 C7 C8 -53.5(4) . . . . ?
C5A C4A C3A C2A 0.3(5) . . . . ?
C5A C4A C1 F2 -107.6(11) . . . . ?
C5A C4A C1 F6 7.2(14) . . . . ?
C5A C4A C1 F4 127.2(16) . . . . ?
C5A C4A C1 F1 -96.1(10) . . . . ?
C5A C4A C1 F5 26.8(18) . . . . ?
C5A C4A C1 F3 150.2(12) . . . . ?
C1 C4A C3A C2A 179.4(3) . . . . ?
C1 C4A C5A C6A -178.7(3) . . . . ?
C11 C6 C7 C8 -172.1(3) . . . . ?
C10 C6 C7 C8 67.8(4) . . . . ?

_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
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMFA'
####################################################################### 
# 
# 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_4a_pani72_ccl4
_database_code_depnum_ccdc_archive 'CCDC 2340418'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
1-(1-hydroxy-4-methyl-2-(4-nitrophenyl)-4,5-dihydro-1H-imidazol-5-yl)ethan-1-one
_chemical_formula_moiety         'C12 H11 N3 O4'
_chemical_formula_sum            'C12 H11 N3 O4'
_chemical_formula_weight         261.24
_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'

_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                   6.2902(6)
_cell_length_b                   7.3546(7)
_cell_length_c                   12.9978(11)
_cell_angle_alpha                85.350(7)
_cell_angle_beta                 88.976(7)
_cell_angle_gamma                83.526(7)
_cell_volume                     595.47(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      27.9230
_cell_measurement_theta_min      3.0840
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_preparation       'chemical sythesis'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Carbon tetrachloride'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6217
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         2.796
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00   60.00    --    0.00   0.00  45.00  180
  2  ω    -30.00  90.00   1.00   60.00    --    0.00  72.00  45.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       'ω 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                1663
_reflns_number_total             2379
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.028
_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)+(0.0699P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1401
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
N1 N 0.1909(2) 0.20625(19) 0.85884(11) 0.0469(4) Uani 1 1 d . . . . .
C1A C -0.0400(3) 0.2624(2) 1.01476(13) 0.0439(4) Uani 1 1 d . . . . .
C2 C 0.0077(3) 0.2684(2) 0.90412(12) 0.0438(4) Uani 1 1 d . . . . .
N3 N -0.1338(2) 0.3403(2) 0.83053(11) 0.0539(4) Uani 1 1 d . . . . .
C4A C -0.1521(3) 0.2601(2) 1.22015(13) 0.0525(5) Uani 1 1 d . . . . .
O3 O 0.3735(2) 0.1305(2) 0.90884(11) 0.0750(5) Uani 1 1 d . . . . .
H3 H 0.462606 0.092947 0.866470 0.113 Uiso 1 1 calc R U . . .
C2A C 0.1038(3) 0.1836(3) 1.09043(14) 0.0552(5) Uani 1 1 d . . . . .
H2A H 0.238973 0.131706 1.071352 0.066 Uiso 1 1 calc R U . . .
C3A C 0.0469(3) 0.1822(3) 1.19337(14) 0.0600(5) Uani 1 1 d . . . . .
H3A H 0.142428 0.129066 1.243904 0.072 Uiso 1 1 calc R U . . .
C5A C -0.2987(3) 0.3396(3) 1.14799(15) 0.0587(5) Uani 1 1 d . . . . .
H5A H -0.432808 0.392241 1.168080 0.070 Uiso 1 1 calc R U . . .
C6A C -0.2417(3) 0.3392(3) 1.04526(14) 0.0553(5) Uani 1 1 d . . . . .
H6A H -0.339392 0.391030 0.995374 0.066 Uiso 1 1 calc R U . . .
O4 O 0.5088(3) 0.0861(2) 0.72535(12) 0.0837(5) Uani 1 1 d . . . . .
C5 C 0.1723(3) 0.2370(2) 0.75229(13) 0.0472(4) Uani 1 1 d . . . . .
C4 C -0.0338(3) 0.3212(3) 0.73888(13) 0.0522(5) Uani 1 1 d . . . . .
O1 O -0.0888(3) 0.1719(3) 1.39266(12) 0.0990(6) Uani 1 1 d . . . . .
N2 N -0.2104(3) 0.2584(3) 1.33050(13) 0.0690(5) Uani 1 1 d . . . . .
O2 O -0.3763(3) 0.3435(3) 1.35470(13) 0.1077(7) Uani 1 1 d . . . . .
C6 C 0.3471(3) 0.1732(3) 0.68629(15) 0.0570(5) Uani 1 1 d . . . . .
C7 C 0.3315(4) 0.2129(3) 0.57200(16) 0.0748(6) Uani 1 1 d . . . . .
H7A H 0.319666 0.343209 0.555317 0.112 Uiso 1 1 calc R U . . .
H7B H 0.207478 0.165012 0.547674 0.112 Uiso 1 1 calc R U . . .
H7C H 0.457343 0.156041 0.539525 0.112 Uiso 1 1 calc R U . . .
C8 C -0.1460(3) 0.3883(4) 0.63999(16) 0.0774(7) Uani 1 1 d . . . . .
H8A H -0.284597 0.449606 0.655087 0.116 Uiso 1 1 calc R U . . .
H8B H -0.161923 0.285853 0.600551 0.116 Uiso 1 1 calc R U . . .
H8C H -0.063363 0.472296 0.600965 0.116 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
N1 C2 1.336(2) . ?
N1 O3 1.3695(18) . ?
N1 C5 1.390(2) . ?
C1A C2 1.462(2) . ?
C1A C2A 1.394(2) . ?
C1A C6A 1.393(2) . ?
C2 N3 1.352(2) . ?
N3 C4 1.347(2) . ?
C4A C3A 1.368(3) . ?
C4A C5A 1.375(3) . ?
C4A N2 1.473(2) . ?
O3 H3 0.8200 . ?
C2A H2A 0.9300 . ?
C2A C3A 1.378(3) . ?
C3A H3A 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.376(3) . ?
C6A H6A 0.9300 . ?
O4 C6 1.233(2) . ?
C5 C4 1.380(2) . ?
C5 C6 1.442(3) . ?
C4 C8 1.498(3) . ?
O1 N2 1.213(2) . ?
N2 O2 1.205(2) . ?
C6 C7 1.493(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 O3 125.73(14) . . ?
C2 N1 C5 109.70(14) . . ?
O3 N1 C5 124.51(14) . . ?
C2A C1A C2 123.70(16) . . ?
C6A C1A C2 117.56(16) . . ?
C6A C1A C2A 118.74(16) . . ?
N1 C2 C1A 127.20(15) . . ?
N1 C2 N3 109.06(15) . . ?
N3 C2 C1A 123.74(15) . . ?
C4 N3 C2 106.77(15) . . ?
C3A C4A C5A 122.41(17) . . ?
C3A C4A N2 118.47(18) . . ?
C5A C4A N2 119.13(17) . . ?
N1 O3 H3 109.5 . . ?
C1A C2A H2A 119.8 . . ?
C3A C2A C1A 120.39(17) . . ?
C3A C2A H2A 119.8 . . ?
C4A C3A C2A 119.06(18) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
C4A C5A H5A 120.9 . . ?
C4A C5A C6A 118.29(17) . . ?
C6A C5A H5A 120.9 . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A C1A 121.10(18) . . ?
C5A C6A H6A 119.4 . . ?
N1 C5 C6 119.92(16) . . ?
C4 C5 N1 103.60(15) . . ?
C4 C5 C6 136.39(17) . . ?
N3 C4 C5 110.87(16) . . ?
N3 C4 C8 120.76(17) . . ?
C5 C4 C8 128.37(17) . . ?
O1 N2 C4A 118.46(19) . . ?
O2 N2 C4A 118.41(19) . . ?
O2 N2 O1 123.13(19) . . ?
O4 C6 C5 119.25(18) . . ?
O4 C6 C7 120.67(18) . . ?
C5 C6 C7 120.08(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
_geom_hbond_publ_flag
C2A H2A O3 0.93 2.26 2.908(2) 126.1 . yes

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
N1 C2 N3 C4 -0.1(2) . . . . ?
N1 C5 C4 N3 -0.1(2) . . . . ?
N1 C5 C4 C8 179.6(2) . . . . ?
N1 C5 C6 O4 2.6(3) . . . . ?
N1 C5 C6 C7 -177.39(17) . . . . ?
C1A C2 N3 C4 -179.86(16) . . . . ?
C1A C2A C3A C4A -0.4(3) . . . . ?
C2 N1 C5 C4 0.04(19) . . . . ?
C2 N1 C5 C6 -177.00(15) . . . . ?
C2 C1A C2A C3A -179.66(17) . . . . ?
C2 C1A C6A C5A -179.74(17) . . . . ?
C2 N3 C4 C5 0.1(2) . . . . ?
C2 N3 C4 C8 -179.65(18) . . . . ?
C4A C5A C6A C1A -0.7(3) . . . . ?
O3 N1 C2 C1A -2.8(3) . . . . ?
O3 N1 C2 N3 177.44(16) . . . . ?
O3 N1 C5 C4 -177.43(16) . . . . ?
O3 N1 C5 C6 5.5(3) . . . . ?
C2A C1A C2 N1 -1.7(3) . . . . ?
C2A C1A C2 N3 178.11(16) . . . . ?
C2A C1A C6A C5A 0.6(3) . . . . ?
C3A C4A C5A C6A 0.3(3) . . . . ?
C3A C4A N2 O1 -7.4(3) . . . . ?
C3A C4A N2 O2 172.3(2) . . . . ?
C5A C4A C3A C2A 0.2(3) . . . . ?
C5A C4A N2 O1 172.62(19) . . . . ?
C5A C4A N2 O2 -7.7(3) . . . . ?
C6A C1A C2 N1 178.72(17) . . . . ?
C6A C1A C2 N3 -1.5(3) . . . . ?
C6A C1A C2A C3A 0.0(3) . . . . ?
C5 N1 C2 C1A 179.81(16) . . . . ?
C5 N1 C2 N3 0.0(2) . . . . ?
C4 C5 C6 O4 -173.3(2) . . . . ?
C4 C5 C6 C7 6.8(3) . . . . ?
N2 C4A C3A C2A -179.73(18) . . . . ?
N2 C4A C5A C6A -179.71(17) . . . . ?
C6 C5 C4 N3 176.2(2) . . . . ?
C6 C5 C4 C8 -4.1(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_4c_pani114_phme
_database_code_depnum_ccdc_archive 'CCDC 2331165'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
'1-(1-hydroxy-4-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazol-5-yl)ethan-1-one 4-acetyl-5-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide'
_chemical_formula_moiety         'C13 H11 F3 N2 O2'
_chemical_formula_sum            'C13 H11 F3 N2 O2'
_chemical_formula_weight         284.24
_chemical_absolute_configuration .
_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   15.7230(16)
_cell_length_b                   14.3769(9)
_cell_length_c                   23.665(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.339(10)
_cell_angle_gamma                90
_cell_volume                     5159.0(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3313
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      25.1670
_cell_measurement_theta_min      2.9380
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69583
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2336
_exptl_crystal_preparation       'chemical sythesis'
_exptl_crystal_recrystallization_method 'slow evaporation toluene solution'
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16053
_diffrn_reflns_point_group_measured_fraction_full 0.903
_diffrn_reflns_point_group_measured_fraction_max 0.736
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.227
_diffrn_reflns_theta_min         2.805
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00  240.00    --    0.00   0.00  45.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                5585
_reflns_number_total             9353
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     836
_refine_ls_number_reflns         9353
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.001
_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)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F6-C1 \\sim F5-C1
 with sigma of 0.02
 F4-C1 \\sim F3-C1
 with sigma of 0.02
 F2-C1 \\sim F1-C1
 with sigma of 0.02
 F18-C1D \\sim F13-C1D
 with sigma of 0.02
 F16-C1D \\sim F17-C1D
 with sigma of 0.02
 F14-C1D \\sim F15-C1D
 with sigma of 0.02
 F9-C1B \\sim F10-C1B
 with sigma of 0.02
 F7-C1B \\sim F8-C1B
 with sigma of 0.02
 F11-C1B \\sim F12-C1B
 with sigma of 0.02
 F22-C1C \\sim F21-C1C
 with sigma of 0.02
 F20-C1C \\sim F19-C1C
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F13, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F15, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F17, C1D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F12, C1B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(F3)=Sof(F1)=Sof(F5)=1-FVAR(1)
 Sof(F6)=Sof(F2)=Sof(F4)=FVAR(1)
 Sof(F13)=Sof(F15)=Sof(F17)=1-FVAR(2)
 Sof(F18)=Sof(F14)=Sof(F16)=FVAR(2)
 Sof(F12)=Sof(F8)=Sof(F10)=1-FVAR(3)
 Sof(F11)=Sof(F9)=Sof(F7)=FVAR(3)
 Sof(F21)=Sof(F19)=1-FVAR(4)
 Sof(F20)=Sof(F22)=FVAR(4)
5.a Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C3AD(H3AD), C6AB(H6AB), C2AD(H2AD), C6AC(H6AC), C5A(H5A),
 C2AC(H2AC), C6AD(H6AD), C5AC(H5AC), C5AD(H5AD), C2A(H2A), C3AC(H3AC),
 C5AB(H5AB), C2AB(H2AB), C3AB(H3AB), C3A(H3A)
5.b Idealised Me refined as rotating group:
 C7C(H7CA,H7CB,H7CC), C01T(H01A,H01B,H01C), C7D(H7DA,H7DB,H7DC), C7(H7A,H7B,
 H7C), C8B(H8BA,H8BB,H8BC), C8(H8A,H8B,H8C), C7B(H7BA,H7BB,H7BC), C8D(H8DA,H8DB,
 H8DC)
5.c Idealised tetrahedral OH refined as rotating group:
 O3B(H3B), O3D(H3D), O3(H3), O3C(H3C)
;
_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
F23 F 0.4211(3) 0.5189(3) 0.6426(2) 0.1294(15) Uani 1 1 d . . . . .
F18 F 0.6408(18) -0.3527(14) 0.4741(8) 0.131(7) Uani 0.58(4) 1 d D . P A 1
O3B O 0.5304(3) 0.3380(3) 0.86088(18) 0.0953(14) Uani 1 1 d . . . . .
H3B H 0.542770 0.390086 0.874694 0.143 Uiso 1 1 calc R U . . .
O3D O 0.6036(3) 0.1272(3) 0.48006(17) 0.0872(12) Uani 1 1 d . . . . .
H3D H 0.584486 0.178872 0.468620 0.131 Uiso 1 1 calc R U . . .
O4 O 0.9182(3) 0.6931(3) 0.9921(2) 0.1060(15) Uani 1 1 d . . . . .
N1 N 0.8442(3) 0.5246(3) 0.95065(17) 0.0589(11) Uani 1 1 d . . . . .
N1D N 0.6695(3) 0.1359(3) 0.53080(18) 0.0612(11) Uani 1 1 d . . . . .
F20 F 0.5496(13) 0.5461(11) 0.6299(7) 0.101(5) Uani 0.61(8) 1 d D . P B 1
O3 O 0.9160(3) 0.5156(3) 0.99780(19) 0.0938(13) Uani 1 1 d . . . . .
H3 H 0.940396 0.566187 1.005516 0.141 Uiso 1 1 calc R U . . .
N1B N 0.4564(3) 0.3427(3) 0.81506(18) 0.0629(11) Uani 1 1 d . . . . .
N3C N 0.6625(3) 0.0904(3) 0.7448(2) 0.0760(13) Uani 1 1 d . . . . .
O4B O 0.4977(4) 0.5124(3) 0.8671(2) 0.1057(15) Uani 1 1 d . . . . .
O4D O 0.5988(3) 0.3043(3) 0.4867(2) 0.1036(14) Uani 1 1 d . . . . .
F11 F 0.4992(9) -0.1651(8) 0.7667(5) 0.123(3) Uani 0.83(3) 1 d D . P C 1
N3D N 0.7751(3) 0.1011(3) 0.6082(2) 0.0864(14) Uani 1 1 d . . . . .
F22 F 0.5206(16) 0.5542(9) 0.7129(4) 0.103(5) Uani 0.61(8) 1 d D . P B 1
O3C O 0.5113(3) 0.0520(3) 0.60851(19) 0.1025(15) Uani 1 1 d . . . . .
H3C H 0.495399 -0.000878 0.597664 0.154 Uiso 1 1 calc R U . . .
N3 N 0.7309(3) 0.4899(3) 0.87795(19) 0.0739(13) Uani 1 1 d . . . . .
O4C O 0.5269(3) -0.1239(3) 0.6124(2) 0.1042(14) Uani 1 1 d . . . . .
C5D C 0.6973(4) 0.2198(3) 0.5584(2) 0.0675(14) Uani 1 1 d . . . . .
N1C N 0.5735(3) 0.0482(3) 0.66137(18) 0.0689(12) Uani 1 1 d . . . . .
C5C C 0.6106(3) -0.0335(4) 0.6874(2) 0.0667(14) Uani 1 1 d . . . . .
N3B N 0.3524(3) 0.2994(3) 0.7385(2) 0.0734(12) Uani 1 1 d . . . . .
C2D C 0.7161(3) 0.0663(3) 0.5611(2) 0.0603(13) Uani 1 1 d . . . . .
C6A C 0.7545(4) 0.2932(4) 0.8970(3) 0.0759(16) Uani 1 1 d . . . . .
H6A H 0.709619 0.315484 0.865937 0.091 Uiso 1 1 calc R U . . .
C1A C 0.8087(3) 0.3556(3) 0.9344(2) 0.0583(12) Uani 1 1 d . . . . .
F14 F 0.6359(14) -0.3612(13) 0.5611(7) 0.120(6) Uani 0.58(4) 1 d D . P A 1
C1AD C 0.7056(3) -0.0343(3) 0.5475(2) 0.0594(13) Uani 1 1 d . . . . .
C1C C 0.5069(4) 0.5067(5) 0.6645(3) 0.0795(17) Uani 1 1 d D . . . .
C3AD C 0.6302(4) -0.1665(4) 0.4967(2) 0.0728(15) Uani 1 1 d . . . . .
H3AD H 0.584089 -0.191146 0.467423 0.087 Uiso 1 1 calc R U . . .
C2B C 0.4216(3) 0.2700(4) 0.7810(2) 0.0622(13) Uani 1 1 d . . . . .
C2 C 0.7955(3) 0.4548(4) 0.9223(2) 0.0594(13) Uani 1 1 d . . . . .
C1AC C 0.5778(3) 0.2196(4) 0.6844(2) 0.0622(13) Uani 1 1 d . . . . .
C4AC C 0.5312(3) 0.4064(4) 0.6724(3) 0.0660(13) Uani 1 1 d . . . . .
C6 C 0.8568(4) 0.6948(4) 0.9470(3) 0.0744(16) Uani 1 1 d . . . . .
C5 C 0.8137(3) 0.6088(3) 0.9243(2) 0.0588(13) Uani 1 1 d . . . . .
F6 F 0.7724(18) 0.0152(15) 0.957(2) 0.23(2) Uani 0.38(3) 1 d D . P D 1
C6B C 0.4348(4) 0.5098(4) 0.8233(3) 0.0754(15) Uani 1 1 d . . . . .
C6AB C 0.4156(4) 0.1113(4) 0.7430(3) 0.0731(15) Uani 1 1 d . . . . .
H6AB H 0.384531 0.135020 0.706843 0.088 Uiso 1 1 calc R U . . .
F16 F 0.7590(9) -0.3705(10) 0.5408(7) 0.110(5) Uani 0.58(4) 1 d D . P A 1
C6D C 0.6564(4) 0.3056(4) 0.5329(3) 0.0745(15) Uani 1 1 d . . . . .
C2AD C 0.6384(4) -0.0714(4) 0.5041(2) 0.0687(15) Uani 1 1 d . . . . .
H2AD H 0.598084 -0.032178 0.479404 0.082 Uiso 1 1 calc R U . . .
C2C C 0.6046(3) 0.1211(4) 0.6956(2) 0.0654(14) Uani 1 1 d . . . . .
C6AC C 0.6113(4) 0.2821(4) 0.7293(2) 0.0694(14) Uani 1 1 d . . . . .
H6AC H 0.650243 0.261451 0.763790 0.083 Uiso 1 1 calc R U . . .
F2 F 0.913(5) 0.0394(18) 1.000(2) 0.28(3) Uani 0.38(3) 1 d D . P D 1
C5A C 0.7660(4) 0.1982(4) 0.9050(3) 0.0820(17) Uani 1 1 d . . . . .
H5A H 0.728879 0.157317 0.879462 0.098 Uiso 1 1 calc R U . . .
C1D C 0.6799(5) -0.3285(4) 0.5268(3) 0.0887(19) Uani 1 1 d D . . . .
C1AB C 0.4478(3) 0.1719(3) 0.7897(2) 0.0576(12) Uani 1 1 d . . . . .
F4 F 0.868(2) 0.0213(17) 0.9159(8) 0.113(10) Uani 0.38(3) 1 d D . P D 1
C4C C 0.6669(3) -0.0036(4) 0.7396(2) 0.0723(15) Uani 1 1 d . . . . .
C2AC C 0.5218(3) 0.2520(4) 0.6329(2) 0.0720(15) Uani 1 1 d . . . . .
H2AC H 0.499925 0.210984 0.602107 0.086 Uiso 1 1 calc R U . . .
C5B C 0.4093(4) 0.4220(4) 0.7941(2) 0.0633(14) Uani 1 1 d . . . . .
F9 F 0.5456(12) -0.1477(5) 0.8582(6) 0.187(8) Uani 0.83(3) 1 d D . P C 1
C6C C 0.5856(4) -0.1220(4) 0.6586(3) 0.0782(16) Uani 1 1 d . . . . .
C4B C 0.3445(3) 0.3924(4) 0.7463(3) 0.0751(15) Uani 1 1 d . . . . .
C6AD C 0.7672(4) -0.0934(4) 0.5829(3) 0.0787(16) Uani 1 1 d . . . . .
H6AD H 0.814104 -0.068899 0.611594 0.094 Uiso 1 1 calc R U . . .
C5AC C 0.5875(3) 0.3744(4) 0.7233(3) 0.0716(15) Uani 1 1 d . . . . .
H5AC H 0.609836 0.415398 0.754056 0.086 Uiso 1 1 calc R U . . .
C5AD C 0.7590(4) -0.1883(4) 0.5754(3) 0.0830(18) Uani 1 1 d . . . . .
H5AD H 0.799949 -0.227696 0.599358 0.100 Uiso 1 1 calc R U . . .
C4AD C 0.6906(4) -0.2250(3) 0.5327(2) 0.0646(14) Uani 1 1 d . . . . .
C4 C 0.7415(4) 0.5827(4) 0.8789(2) 0.0676(14) Uani 1 1 d . . . . .
C4A C 0.8301(4) 0.1649(4) 0.9494(2) 0.0705(15) Uani 1 1 d . . . . .
C2A C 0.8736(4) 0.3200(4) 0.9806(3) 0.0766(16) Uani 1 1 d . . . . .
H2A H 0.910635 0.360146 1.006852 0.092 Uiso 1 1 calc R U . . .
C3AC C 0.4981(4) 0.3439(4) 0.6269(3) 0.0778(16) Uani 1 1 d . . . . .
H3AC H 0.459778 0.364713 0.592225 0.093 Uiso 1 1 calc R U . . .
C7C C 0.6271(5) -0.2102(4) 0.6855(3) 0.0920(19) Uani 1 1 d . . . . .
H7CA H 0.622177 -0.256385 0.655505 0.138 Uiso 1 1 calc R U . . .
H7CB H 0.597572 -0.231654 0.713742 0.138 Uiso 1 1 calc R U . . .
H7CC H 0.688197 -0.199388 0.704523 0.138 Uiso 1 1 calc R U . . .
C01T C 0.7243(4) -0.0593(5) 0.7892(3) 0.102(2) Uani 1 1 d . . . . .
H01A H 0.746980 -0.112773 0.773735 0.153 Uiso 1 1 calc R U . . .
H01B H 0.689894 -0.079278 0.815047 0.153 Uiso 1 1 calc R U . . .
H01C H 0.772379 -0.021458 0.810540 0.153 Uiso 1 1 calc R U . . .
C4AB C 0.4764(4) -0.0183(4) 0.8030(3) 0.0723(15) Uani 1 1 d . . . . .
F7 F 0.4082(10) -0.1573(4) 0.8165(9) 0.152(6) Uani 0.83(3) 1 d D . P C 1
C5AB C 0.4293(4) 0.0166(4) 0.7496(3) 0.0779(16) Uani 1 1 d . . . . .
H5AB H 0.406981 -0.023311 0.718218 0.093 Uiso 1 1 calc R U . . .
C1B C 0.4840(5) -0.1211(4) 0.8120(3) 0.0905(19) Uani 1 1 d D . . . .
C4D C 0.7631(4) 0.1940(4) 0.6064(3) 0.0879(19) Uani 1 1 d . . . . .
C2AB C 0.4994(3) 0.1362(4) 0.8414(3) 0.0729(15) Uani 1 1 d . . . . .
H2AB H 0.525382 0.176100 0.871977 0.087 Uiso 1 1 calc R U . . .
C7D C 0.6842(5) 0.3973(4) 0.5642(4) 0.102(2) Uani 1 1 d . . . . .
H7DA H 0.742404 0.413262 0.561681 0.153 Uiso 1 1 calc R U . . .
H7DB H 0.684177 0.391476 0.604562 0.153 Uiso 1 1 calc R U . . .
H7DC H 0.643597 0.445243 0.545998 0.153 Uiso 1 1 calc R U . . .
C1 C 0.8450(7) 0.0615(4) 0.9573(3) 0.094(2) Uani 1 1 d D . . . .
C3AB C 0.5130(4) 0.0407(4) 0.8481(3) 0.0749(16) Uani 1 1 d . . . . .
H3AB H 0.547078 0.017064 0.883461 0.090 Uiso 1 1 calc R U . . .
C7 C 0.8286(5) 0.7849(4) 0.9171(3) 0.100(2) Uani 1 1 d . . . . .
H7A H 0.863070 0.834380 0.939054 0.150 Uiso 1 1 calc R U . . .
H7B H 0.767354 0.795204 0.914438 0.150 Uiso 1 1 calc R U . . .
H7C H 0.837164 0.783284 0.878384 0.150 Uiso 1 1 calc R U . . .
C8B C 0.2707(4) 0.4456(5) 0.7060(3) 0.107(2) Uani 1 1 d . . . . .
H8BA H 0.294632 0.489787 0.684010 0.160 Uiso 1 1 calc R U . . .
H8BB H 0.237543 0.477816 0.728725 0.160 Uiso 1 1 calc R U . . .
H8BC H 0.232635 0.403194 0.679663 0.160 Uiso 1 1 calc R U . . .
C8 C 0.6782(5) 0.6430(4) 0.8358(3) 0.105(2) Uani 1 1 d . . . . .
H8A H 0.708972 0.674452 0.811328 0.157 Uiso 1 1 calc R U . . .
H8B H 0.652784 0.687963 0.856451 0.157 Uiso 1 1 calc R U . . .
H8C H 0.632290 0.605052 0.811877 0.157 Uiso 1 1 calc R U . . .
C7B C 0.3864(5) 0.5980(4) 0.8008(3) 0.099(2) Uani 1 1 d . . . . .
H7BA H 0.387314 0.607727 0.760855 0.148 Uiso 1 1 calc R U . . .
H7BB H 0.414420 0.649510 0.824290 0.148 Uiso 1 1 calc R U . . .
H7BC H 0.326374 0.593180 0.802923 0.148 Uiso 1 1 calc R U . . .
C8D C 0.8209(6) 0.2549(6) 0.6548(4) 0.147(3) Uani 1 1 d . . . . .
H8DA H 0.784046 0.294302 0.670973 0.221 Uiso 1 1 calc R U . . .
H8DB H 0.859076 0.292570 0.638596 0.221 Uiso 1 1 calc R U . . .
H8DC H 0.855851 0.215888 0.685080 0.221 Uiso 1 1 calc R U . . .
C3A C 0.8837(4) 0.2239(4) 0.9880(3) 0.0839(18) Uani 1 1 d . . . . .
H3A H 0.927103 0.200081 1.019352 0.101 Uiso 1 1 calc R U . . .
F3 F 0.903(3) 0.0302(13) 0.9345(18) 0.230(14) Uani 0.62(3) 1 d D . P D 2
F1 F 0.8645(11) 0.0338(9) 1.0112(5) 0.112(5) Uani 0.62(3) 1 d D . P D 2
F5 F 0.7716(12) 0.0146(8) 0.9348(7) 0.165(10) Uani 0.62(3) 1 d D . P D 2
F13 F 0.605(3) -0.358(2) 0.536(3) 0.23(2) Uani 0.42(4) 1 d D . P A 2
F15 F 0.740(3) -0.3771(16) 0.561(2) 0.222(18) Uani 0.42(4) 1 d D . P A 2
F17 F 0.666(3) -0.362(2) 0.4739(11) 0.154(14) Uani 0.42(4) 1 d D . P A 2
F12 F 0.462(7) -0.179(4) 0.769(2) 0.17(4) Uani 0.17(3) 1 d D . P C 2
F8 F 0.465(3) -0.1563(19) 0.8578(17) 0.098(17) Uani 0.17(3) 1 d D . P C 2
F10 F 0.5701(15) -0.141(2) 0.826(2) 0.102(14) Uani 0.17(3) 1 d D . P C 2
F21 F 0.543(4) 0.558(2) 0.7103(13) 0.172(16) Uani 0.39(8) 1 d D . P B 2
F19 F 0.527(5) 0.553(2) 0.621(2) 0.172(17) Uani 0.39(8) 1 d D . P 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
F23 C1C 1.321(7) . ?
F18 C1D 1.283(16) . ?
O3B H3B 0.8200 . ?
O3B N1B 1.366(5) . ?
O3D H3D 0.8200 . ?
O3D N1D 1.369(5) . ?
O4 C6 1.236(7) . ?
N1 O3 1.367(5) . ?
N1 C2 1.332(6) . ?
N1 C5 1.388(6) . ?
N1D C5D 1.386(6) . ?
N1D C2D 1.332(6) . ?
F20 C1C 1.317(13) . ?
O3 H3 0.8200 . ?
N1B C2B 1.345(7) . ?
N1B C5B 1.378(6) . ?
N3C C2C 1.347(6) . ?
N3C C4C 1.361(7) . ?
O4B C6B 1.228(7) . ?
O4D C6D 1.222(6) . ?
F11 C1B 1.319(10) . ?
N3D C2D 1.343(6) . ?
N3D C4D 1.349(8) . ?
F22 C1C 1.303(11) . ?
O3C H3C 0.8200 . ?
O3C N1C 1.371(5) . ?
N3 C2 1.350(6) . ?
N3 C4 1.344(7) . ?
O4C C6C 1.231(6) . ?
C5D C6D 1.448(8) . ?
C5D C4D 1.369(8) . ?
N1C C5C 1.381(7) . ?
N1C C2C 1.336(7) . ?
C5C C4C 1.384(8) . ?
C5C C6C 1.447(8) . ?
N3B C2B 1.341(7) . ?
N3B C4B 1.360(7) . ?
C2D C1AD 1.480(7) . ?
C6A H6A 0.9300 . ?
C6A C1A 1.384(7) . ?
C6A C5A 1.385(7) . ?
C1A C2 1.459(7) . ?
C1A C2A 1.382(7) . ?
F14 C1D 1.287(15) . ?
C1AD C2AD 1.373(7) . ?
C1AD C6AD 1.390(7) . ?
C1C C4AC 1.492(8) . ?
C1C F21 1.310(18) . ?
C1C F19 1.33(2) . ?
C3AD H3AD 0.9300 . ?
C3AD C2AD 1.380(7) . ?
C3AD C4AD 1.381(7) . ?
C2B C1AB 1.468(7) . ?
C1AC C2C 1.482(8) . ?
C1AC C6AC 1.383(7) . ?
C1AC C2AC 1.382(7) . ?
C4AC C5AC 1.372(7) . ?
C4AC C3AC 1.394(8) . ?
C6 C5 1.443(8) . ?
C6 C7 1.486(8) . ?
C5 C4 1.392(7) . ?
F6 C1 1.318(19) . ?
C6B C5B 1.445(8) . ?
C6B C7B 1.502(8) . ?
C6AB H6AB 0.9300 . ?
C6AB C1AB 1.394(7) . ?
C6AB C5AB 1.381(7) . ?
F16 C1D 1.344(13) . ?
C6D C7D 1.518(8) . ?
C2AD H2AD 0.9300 . ?
C6AC H6AC 0.9300 . ?
C6AC C5AC 1.375(8) . ?
F2 C1 1.30(2) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.338(8) . ?
C1D C4AD 1.500(8) . ?
C1D F13 1.32(3) . ?
C1D F15 1.27(2) . ?
C1D F17 1.30(2) . ?
C1AB C2AB 1.375(7) . ?
F4 C1 1.267(18) . ?
C4C C01T 1.509(7) . ?
C2AC H2AC 0.9300 . ?
C2AC C3AC 1.370(8) . ?
C5B C4B 1.374(7) . ?
F9 C1B 1.312(10) . ?
C6C C7C 1.489(8) . ?
C4B C8B 1.502(8) . ?
C6AD H6AD 0.9300 . ?
C6AD C5AD 1.378(8) . ?
C5AC H5AC 0.9300 . ?
C5AD H5AD 0.9300 . ?
C5AD C4AD 1.371(8) . ?
C4 C8 1.498(7) . ?
C4A C1 1.509(8) . ?
C4A C3A 1.363(8) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.397(8) . ?
C3AC H3AC 0.9300 . ?
C7C H7CA 0.9600 . ?
C7C H7CB 0.9600 . ?
C7C H7CC 0.9600 . ?
C01T H01A 0.9600 . ?
C01T H01B 0.9600 . ?
C01T H01C 0.9600 . ?
C4AB C5AB 1.380(7) . ?
C4AB C1B 1.493(8) . ?
C4AB C3AB 1.366(8) . ?
F7 C1B 1.330(11) . ?
C5AB H5AB 0.9300 . ?
C1B F12 1.30(3) . ?
C1B F8 1.30(2) . ?
C1B F10 1.34(2) . ?
C4D C8D 1.535(9) . ?
C2AB H2AB 0.9300 . ?
C2AB C3AB 1.392(7) . ?
C7D H7DA 0.9600 . ?
C7D H7DB 0.9600 . ?
C7D H7DC 0.9600 . ?
C1 F3 1.259(15) . ?
C1 F1 1.292(12) . ?
C1 F5 1.320(14) . ?
C3AB H3AB 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7B H7BA 0.9600 . ?
C7B H7BB 0.9600 . ?
C7B H7BC 0.9600 . ?
C8D H8DA 0.9600 . ?
C8D H8DB 0.9600 . ?
C8D H8DC 0.9600 . ?
C3A H3A 0.9300 . ?

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
N1B O3B H3B 109.5 . . ?
N1D O3D H3D 109.5 . . ?
O3 N1 C5 124.2(4) . . ?
C2 N1 O3 125.5(4) . . ?
C2 N1 C5 110.3(4) . . ?
O3D N1D C5D 124.3(4) . . ?
C2D N1D O3D 125.8(4) . . ?
C2D N1D C5D 109.9(4) . . ?
N1 O3 H3 109.5 . . ?
O3B N1B C5B 126.2(4) . . ?
C2B N1B O3B 124.2(4) . . ?
C2B N1B C5B 109.5(4) . . ?
C2C N3C C4C 106.6(4) . . ?
C2D N3D C4D 106.4(4) . . ?
N1C O3C H3C 109.5 . . ?
C4 N3 C2 107.1(4) . . ?
N1D C5D C6D 119.7(5) . . ?
C4D C5D N1D 103.3(4) . . ?
C4D C5D C6D 137.0(5) . . ?
O3C N1C C5C 123.8(4) . . ?
C2C N1C O3C 125.5(5) . . ?
C2C N1C C5C 110.7(4) . . ?
N1C C5C C4C 103.2(5) . . ?
N1C C5C C6C 120.5(5) . . ?
C4C C5C C6C 136.2(5) . . ?
C2B N3B C4B 107.0(4) . . ?
N1D C2D N3D 109.1(4) . . ?
N1D C2D C1AD 127.1(4) . . ?
N3D C2D C1AD 123.8(4) . . ?
C1A C6A H6A 119.5 . . ?
C1A C6A C5A 121.0(5) . . ?
C5A C6A H6A 119.5 . . ?
C6A C1A C2 118.4(5) . . ?
C2A C1A C6A 117.9(5) . . ?
C2A C1A C2 123.6(5) . . ?
C2AD C1AD C2D 124.2(4) . . ?
C2AD C1AD C6AD 119.2(5) . . ?
C6AD C1AD C2D 116.5(5) . . ?
F23 C1C C4AC 112.3(5) . . ?
F23 C1C F19 93(4) . . ?
F20 C1C F23 109.6(11) . . ?
F20 C1C C4AC 109.8(10) . . ?
F22 C1C F23 100.9(11) . . ?
F22 C1C F20 109.2(12) . . ?
F22 C1C C4AC 114.7(8) . . ?
F21 C1C F23 115(3) . . ?
F21 C1C C4AC 113.4(16) . . ?
F21 C1C F19 102(2) . . ?
F19 C1C C4AC 119(2) . . ?
C2AD C3AD H3AD 120.0 . . ?
C2AD C3AD C4AD 120.0(5) . . ?
C4AD C3AD H3AD 120.0 . . ?
N1B C2B C1AB 127.5(5) . . ?
N3B C2B N1B 108.9(5) . . ?
N3B C2B C1AB 123.4(4) . . ?
N1 C2 N3 108.9(4) . . ?
N1 C2 C1A 127.2(4) . . ?
N3 C2 C1A 123.8(5) . . ?
C6AC C1AC C2C 116.8(5) . . ?
C2AC C1AC C2C 124.3(5) . . ?
C2AC C1AC C6AC 118.9(5) . . ?
C5AC C4AC C1C 121.3(5) . . ?
C5AC C4AC C3AC 119.0(5) . . ?
C3AC C4AC C1C 119.6(5) . . ?
O4 C6 C5 119.2(5) . . ?
O4 C6 C7 119.6(6) . . ?
C5 C6 C7 121.2(6) . . ?
N1 C5 C6 120.5(5) . . ?
N1 C5 C4 103.1(4) . . ?
C4 C5 C6 136.5(5) . . ?
O4B C6B C5B 119.3(5) . . ?
O4B C6B C7B 119.5(6) . . ?
C5B C6B C7B 121.2(6) . . ?
C1AB C6AB H6AB 119.6 . . ?
C5AB C6AB H6AB 119.6 . . ?
C5AB C6AB C1AB 120.9(5) . . ?
O4D C6D C5D 120.1(5) . . ?
O4D C6D C7D 120.0(6) . . ?
C5D C6D C7D 119.9(6) . . ?
C1AD C2AD C3AD 120.5(5) . . ?
C1AD C2AD H2AD 119.7 . . ?
C3AD C2AD H2AD 119.7 . . ?
N3C C2C C1AC 124.2(5) . . ?
N1C C2C N3C 108.9(5) . . ?
N1C C2C C1AC 126.9(5) . . ?
C1AC C6AC H6AC 119.7 . . ?
C5AC C6AC C1AC 120.6(5) . . ?
C5AC C6AC H6AC 119.7 . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A C6A 120.4(5) . . ?
C4A C5A H5A 119.8 . . ?
F18 C1D F14 108.4(15) . . ?
F18 C1D F16 107.0(15) . . ?
F18 C1D C4AD 111.8(11) . . ?
F14 C1D F16 107.4(13) . . ?
F14 C1D C4AD 111.7(10) . . ?
F16 C1D C4AD 110.4(9) . . ?
F13 C1D C4AD 113.1(16) . . ?
F15 C1D C4AD 116.0(13) . . ?
F15 C1D F13 105(2) . . ?
F15 C1D F17 108(3) . . ?
F17 C1D C4AD 116.2(16) . . ?
F17 C1D F13 96(3) . . ?
C6AB C1AB C2B 117.3(5) . . ?
C2AB C1AB C2B 124.1(5) . . ?
C2AB C1AB C6AB 118.5(5) . . ?
N3C C4C C5C 110.7(5) . . ?
N3C C4C C01T 119.4(5) . . ?
C5C C4C C01T 129.8(6) . . ?
C1AC C2AC H2AC 119.7 . . ?
C3AC C2AC C1AC 120.6(5) . . ?
C3AC C2AC H2AC 119.7 . . ?
N1B C5B C6B 119.7(5) . . ?
C4B C5B N1B 104.5(5) . . ?
C4B C5B C6B 135.7(5) . . ?
O4C C6C C5C 118.9(5) . . ?
O4C C6C C7C 120.1(6) . . ?
C5C C6C C7C 121.0(5) . . ?
N3B C4B C5B 110.0(5) . . ?
N3B C4B C8B 119.8(5) . . ?
C5B C4B C8B 130.2(6) . . ?
C1AD C6AD H6AD 120.0 . . ?
C5AD C6AD C1AD 120.1(5) . . ?
C5AD C6AD H6AD 120.0 . . ?
C4AC C5AC C6AC 120.6(5) . . ?
C4AC C5AC H5AC 119.7 . . ?
C6AC C5AC H5AC 119.7 . . ?
C6AD C5AD H5AD 119.8 . . ?
C4AD C5AD C6AD 120.3(5) . . ?
C4AD C5AD H5AD 119.8 . . ?
C3AD C4AD C1D 120.4(5) . . ?
C5AD C4AD C3AD 119.8(5) . . ?
C5AD C4AD C1D 119.8(5) . . ?
N3 C4 C5 110.7(4) . . ?
N3 C4 C8 120.4(5) . . ?
C5 C4 C8 128.9(5) . . ?
C5A C4A C1 120.7(6) . . ?
C5A C4A C3A 120.5(5) . . ?
C3A C4A C1 118.8(6) . . ?
C1A C2A H2A 120.0 . . ?
C1A C2A C3A 120.0(5) . . ?
C3A C2A H2A 120.0 . . ?
C4AC C3AC H3AC 119.8 . . ?
C2AC C3AC C4AC 120.4(5) . . ?
C2AC C3AC H3AC 119.8 . . ?
C6C C7C H7CA 109.5 . . ?
C6C C7C H7CB 109.5 . . ?
C6C C7C H7CC 109.5 . . ?
H7CA C7C H7CB 109.5 . . ?
H7CA C7C H7CC 109.5 . . ?
H7CB C7C H7CC 109.5 . . ?
C4C C01T H01A 109.5 . . ?
C4C C01T H01B 109.5 . . ?
C4C C01T H01C 109.5 . . ?
H01A C01T H01B 109.5 . . ?
H01A C01T H01C 109.5 . . ?
H01B C01T H01C 109.5 . . ?
C5AB C4AB C1B 119.6(5) . . ?
C3AB C4AB C5AB 120.2(5) . . ?
C3AB C4AB C1B 120.2(6) . . ?
C6AB C5AB H5AB 120.3 . . ?
C4AB C5AB C6AB 119.5(5) . . ?
C4AB C5AB H5AB 120.3 . . ?
F11 C1B C4AB 112.6(9) . . ?
F11 C1B F7 103.7(8) . . ?
F9 C1B F11 106.5(11) . . ?
F9 C1B C4AB 114.9(7) . . ?
F9 C1B F7 107.4(10) . . ?
F7 C1B C4AB 111.1(6) . . ?
F12 C1B C4AB 122(3) . . ?
F12 C1B F8 110(3) . . ?
F12 C1B F10 96(5) . . ?
F8 C1B C4AB 118.4(14) . . ?
F8 C1B F10 98.6(19) . . ?
F10 C1B C4AB 106.3(14) . . ?
N3D C4D C5D 111.3(5) . . ?
N3D C4D C8D 119.4(6) . . ?
C5D C4D C8D 129.3(6) . . ?
C1AB C2AB H2AB 119.8 . . ?
C1AB C2AB C3AB 120.5(5) . . ?
C3AB C2AB H2AB 119.8 . . ?
C6D C7D H7DA 109.5 . . ?
C6D C7D H7DB 109.5 . . ?
C6D C7D H7DC 109.5 . . ?
H7DA C7D H7DB 109.5 . . ?
H7DA C7D H7DC 109.5 . . ?
H7DB C7D H7DC 109.5 . . ?
F6 C1 C4A 113.0(13) . . ?
F2 C1 F6 115(3) . . ?
F2 C1 C4A 113.9(14) . . ?
F4 C1 F6 100(2) . . ?
F4 C1 F2 98(3) . . ?
F4 C1 C4A 114.8(13) . . ?
F3 C1 C4A 113.8(11) . . ?
F3 C1 F1 107.7(19) . . ?
F3 C1 F5 107.4(18) . . ?
F1 C1 C4A 114.4(8) . . ?
F1 C1 F5 101.2(10) . . ?
F5 C1 C4A 111.3(10) . . ?
C4AB C3AB C2AB 120.2(6) . . ?
C4AB C3AB H3AB 119.9 . . ?
C2AB C3AB H3AB 119.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4B C8B H8BA 109.5 . . ?
C4B C8B H8BB 109.5 . . ?
C4B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C4D C8D H8DA 109.5 . . ?
C4D C8D H8DB 109.5 . . ?
C4D C8D H8DC 109.5 . . ?
H8DA C8D H8DB 109.5 . . ?
H8DA C8D H8DC 109.5 . . ?
H8DB C8D H8DC 109.5 . . ?
C4A C3A C2A 120.2(5) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?

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
_geom_hbond_publ_flag
O3B H3B O4B 0.82 1.89 2.572(6) 140.3 . yes
O3D H3D O4D 0.82 1.85 2.553(5) 142.6 . yes
O3 H3 O4 0.82 1.87 2.557(6) 140.6 . yes
O3C H3C O4C 0.82 1.84 2.540(6) 141.8 . yes
C2A H2A O3 0.93 2.25 2.893(7) 125.8 . yes

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
F23 C1C C4AC C5AC -133.6(6) . . . . ?
F23 C1C C4AC C3AC 48.0(8) . . . . ?
F18 C1D C4AD C3AD 29.6(17) . . . . ?
F18 C1D C4AD C5AD -152.6(16) . . . . ?
O3B N1B C2B N3B -176.7(5) . . . . ?
O3B N1B C2B C1AB 8.1(8) . . . . ?
O3B N1B C5B C6B -3.4(8) . . . . ?
O3B N1B C5B C4B 176.7(5) . . . . ?
O3D N1D C5D C6D -0.9(8) . . . . ?
O3D N1D C5D C4D 180.0(5) . . . . ?
O3D N1D C2D N3D 179.8(5) . . . . ?
O3D N1D C2D C1AD -1.6(9) . . . . ?
O4 C6 C5 N1 -4.0(8) . . . . ?
O4 C6 C5 C4 174.8(6) . . . . ?
N1 C5 C4 N3 -0.9(6) . . . . ?
N1 C5 C4 C8 177.3(6) . . . . ?
N1D C5D C6D O4D -1.3(9) . . . . ?
N1D C5D C6D C7D 177.7(5) . . . . ?
N1D C5D C4D N3D 0.1(7) . . . . ?
N1D C5D C4D C8D 179.8(8) . . . . ?
N1D C2D C1AD C2AD -7.3(9) . . . . ?
N1D C2D C1AD C6AD 174.5(5) . . . . ?
F20 C1C C4AC C5AC 104.2(11) . . . . ?
F20 C1C C4AC C3AC -74.2(11) . . . . ?
O3 N1 C2 N3 -179.5(5) . . . . ?
O3 N1 C2 C1A -1.2(9) . . . . ?
O3 N1 C5 C6 -1.4(7) . . . . ?
O3 N1 C5 C4 179.4(5) . . . . ?
N1B C2B C1AB C6AB -167.0(5) . . . . ?
N1B C2B C1AB C2AB 15.1(9) . . . . ?
N1B C5B C4B N3B -0.5(6) . . . . ?
N1B C5B C4B C8B 177.9(6) . . . . ?
O4B C6B C5B N1B -0.8(8) . . . . ?
O4B C6B C5B C4B 179.0(6) . . . . ?
N3D C2D C1AD C2AD 171.2(6) . . . . ?
N3D C2D C1AD C6AD -7.0(8) . . . . ?
F22 C1C C4AC C5AC -19.2(14) . . . . ?
F22 C1C C4AC C3AC 162.4(12) . . . . ?
O3C N1C C5C C4C -178.6(5) . . . . ?
O3C N1C C5C C6C 1.0(8) . . . . ?
O3C N1C C2C N3C 177.9(5) . . . . ?
O3C N1C C2C C1AC 1.1(9) . . . . ?
C5D N1D C2D N3D -0.5(6) . . . . ?
C5D N1D C2D C1AD 178.2(5) . . . . ?
N1C C5C C4C N3C 1.0(6) . . . . ?
N1C C5C C4C C01T 177.2(6) . . . . ?
N1C C5C C6C O4C -4.4(8) . . . . ?
N1C C5C C6C C7C 178.2(5) . . . . ?
C5C N1C C2C N3C 0.0(6) . . . . ?
C5C N1C C2C C1AC -176.9(5) . . . . ?
N3B C2B C1AB C6AB 18.4(8) . . . . ?
N3B C2B C1AB C2AB -159.5(5) . . . . ?
C2D N1D C5D C6D 179.4(5) . . . . ?
C2D N1D C5D C4D 0.2(6) . . . . ?
C2D N3D C4D C5D -0.4(8) . . . . ?
C2D N3D C4D C8D 179.9(7) . . . . ?
C2D C1AD C2AD C3AD -175.9(6) . . . . ?
C2D C1AD C6AD C5AD 176.1(6) . . . . ?
C6A C1A C2 N1 -175.2(5) . . . . ?
C6A C1A C2 N3 2.9(8) . . . . ?
C6A C1A C2A C3A 0.8(9) . . . . ?
C6A C5A C4A C1 -178.0(7) . . . . ?
C6A C5A C4A C3A 1.5(10) . . . . ?
C1A C6A C5A C4A 0.0(10) . . . . ?
C1A C2A C3A C4A 0.6(10) . . . . ?
F14 C1D C4AD C3AD -92.1(12) . . . . ?
F14 C1D C4AD C5AD 85.7(12) . . . . ?
C1AD C6AD C5AD C4AD 0.7(10) . . . . ?
C1C C4AC C5AC C6AC -178.1(5) . . . . ?
C1C C4AC C3AC C2AC 178.2(6) . . . . ?
C2B N1B C5B C6B -179.5(5) . . . . ?
C2B N1B C5B C4B 0.6(6) . . . . ?
C2B N3B C4B C5B 0.2(6) . . . . ?
C2B N3B C4B C8B -178.4(5) . . . . ?
C2B C1AB C2AB C3AB 172.7(5) . . . . ?
C2 N1 C5 C6 -179.4(5) . . . . ?
C2 N1 C5 C4 1.5(6) . . . . ?
C2 N3 C4 C5 0.0(6) . . . . ?
C2 N3 C4 C8 -178.3(5) . . . . ?
C2 C1A C2A C3A -177.8(6) . . . . ?
C1AC C6AC C5AC C4AC -1.0(8) . . . . ?
C1AC C2AC C3AC C4AC 0.8(9) . . . . ?
C6 C5 C4 N3 -179.8(6) . . . . ?
C6 C5 C4 C8 -1.6(11) . . . . ?
C5 N1 C2 N3 -1.6(6) . . . . ?
C5 N1 C2 C1A 176.8(5) . . . . ?
C6B C5B C4B N3B 179.7(6) . . . . ?
C6B C5B C4B C8B -1.9(11) . . . . ?
C6AB C1AB C2AB C3AB -5.2(8) . . . . ?
F16 C1D C4AD C3AD 148.6(10) . . . . ?
F16 C1D C4AD C5AD -33.7(12) . . . . ?
C6D C5D C4D N3D -178.8(7) . . . . ?
C6D C5D C4D C8D 0.9(13) . . . . ?
C2AD C1AD C6AD C5AD -2.1(9) . . . . ?
C2AD C3AD C4AD C1D 177.1(6) . . . . ?
C2AD C3AD C4AD C5AD -0.6(9) . . . . ?
C2C N3C C4C C5C -1.1(6) . . . . ?
C2C N3C C4C C01T -177.7(5) . . . . ?
C2C N1C C5C C4C -0.6(6) . . . . ?
C2C N1C C5C C6C 179.0(5) . . . . ?
C2C C1AC C6AC C5AC -177.9(5) . . . . ?
C2C C1AC C2AC C3AC 177.9(5) . . . . ?
C6AC C1AC C2C N3C -3.8(8) . . . . ?
C6AC C1AC C2C N1C 172.6(5) . . . . ?
C6AC C1AC C2AC C3AC -1.5(8) . . . . ?
C5A C6A C1A C2 177.6(6) . . . . ?
C5A C6A C1A C2A -1.1(9) . . . . ?
C5A C4A C1 F6 -51(3) . . . . ?
C5A C4A C1 F2 176(5) . . . . ?
C5A C4A C1 F4 63.4(19) . . . . ?
C5A C4A C1 F3 95(3) . . . . ?
C5A C4A C1 F1 -140.7(11) . . . . ?
C5A C4A C1 F5 -26.7(14) . . . . ?
C5A C4A C3A C2A -1.8(10) . . . . ?
C1AB C6AB C5AB C4AB -0.8(9) . . . . ?
C1AB C2AB C3AB C4AB 1.2(9) . . . . ?
C4C N3C C2C N1C 0.7(6) . . . . ?
C4C N3C C2C C1AC 177.6(5) . . . . ?
C4C C5C C6C O4C 175.0(7) . . . . ?
C4C C5C C6C C7C -2.4(11) . . . . ?
C2AC C1AC C2C N3C 176.8(5) . . . . ?
C2AC C1AC C2C N1C -6.9(9) . . . . ?
C2AC C1AC C6AC C5AC 1.6(8) . . . . ?
C5B N1B C2B N3B -0.5(6) . . . . ?
C5B N1B C2B C1AB -175.8(5) . . . . ?
C6C C5C C4C N3C -178.5(6) . . . . ?
C6C C5C C4C C01T -2.3(11) . . . . ?
C4B N3B C2B N1B 0.2(6) . . . . ?
C4B N3B C2B C1AB 175.7(5) . . . . ?
C6AD C1AD C2AD C3AD 2.2(8) . . . . ?
C6AD C5AD C4AD C3AD 0.6(9) . . . . ?
C6AD C5AD C4AD C1D -177.1(6) . . . . ?
C5AC C4AC C3AC C2AC -0.2(8) . . . . ?
C4AD C3AD C2AD C1AD -0.8(9) . . . . ?
C4 N3 C2 N1 0.9(6) . . . . ?
C4 N3 C2 C1A -177.4(5) . . . . ?
C2A C1A C2 N1 3.5(9) . . . . ?
C2A C1A C2 N3 -178.5(5) . . . . ?
C3AC C4AC C5AC C6AC 0.3(8) . . . . ?
C5AB C6AB C1AB C2B -173.1(5) . . . . ?
C5AB C6AB C1AB C2AB 5.0(8) . . . . ?
C5AB C4AB C1B F11 42.6(11) . . . . ?
C5AB C4AB C1B F9 164.8(13) . . . . ?
C5AB C4AB C1B F7 -73.1(13) . . . . ?
C5AB C4AB C1B F12 13(6) . . . . ?
C5AB C4AB C1B F8 -129(3) . . . . ?
C5AB C4AB C1B F10 121(2) . . . . ?
C5AB C4AB C3AB C2AB 3.2(9) . . . . ?
C1B C4AB C5AB C6AB 174.2(6) . . . . ?
C1B C4AB C3AB C2AB -174.3(6) . . . . ?
C4D N3D C2D N1D 0.5(7) . . . . ?
C4D N3D C2D C1AD -178.2(5) . . . . ?
C4D C5D C6D O4D 177.5(7) . . . . ?
C4D C5D C6D C7D -3.5(11) . . . . ?
C1 C4A C3A C2A 177.7(7) . . . . ?
C3AB C4AB C5AB C6AB -3.4(9) . . . . ?
C3AB C4AB C1B F11 -139.9(9) . . . . ?
C3AB C4AB C1B F9 -17.7(15) . . . . ?
C3AB C4AB C1B F7 104.4(12) . . . . ?
C3AB C4AB C1B F12 -169(6) . . . . ?
C3AB C4AB C1B F8 48(3) . . . . ?
C3AB C4AB C1B F10 -61(2) . . . . ?
C7 C6 C5 N1 176.1(5) . . . . ?
C7 C6 C5 C4 -5.1(10) . . . . ?
C7B C6B C5B N1B 178.5(5) . . . . ?
C7B C6B C5B C4B -1.7(10) . . . . ?
C3A C4A C1 F6 130(2) . . . . ?
C3A C4A C1 F2 -4(5) . . . . ?
C3A C4A C1 F4 -116.1(17) . . . . ?
C3A C4A C1 F3 -85(3) . . . . ?
C3A C4A C1 F1 39.8(14) . . . . ?
C3A C4A C1 F5 153.8(12) . . . . ?
F13 C1D C4AD C3AD -60(4) . . . . ?
F13 C1D C4AD C5AD 118(4) . . . . ?
F15 C1D C4AD C3AD 179(4) . . . . ?
F15 C1D C4AD C5AD -4(4) . . . . ?
F17 C1D C4AD C3AD 49(2) . . . . ?
F17 C1D C4AD C5AD -133(2) . . . . ?
F21 C1C C4AC C5AC -1(3) . . . . ?
F21 C1C C4AC C3AC -179(3) . . . . ?
F19 C1C C4AC C5AC 119(4) . . . . ?
F19 C1C C4AC C3AC -59(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_semihydrate_4c_pani114_ch3no2
_database_code_depnum_ccdc_archive 'CCDC 2340465'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
'1-(1-hydroxy-4-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazol-5-yl)ethan-1-one 4-acetyl-5-methyl-2-(4-(trifluoromethyl)phenyl)-1H-imidazole 3-oxide hydrate'
_chemical_formula_moiety         '2(C13 H11 F3 N2 O2), H2 O'
_chemical_formula_sum            'C26 H24 F6 N4 O5'
_chemical_formula_weight         586.49
_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                   9.7912(6)
_cell_length_b                   11.5563(9)
_cell_length_c                   12.0456(8)
_cell_angle_alpha                91.342(6)
_cell_angle_beta                 101.399(5)
_cell_angle_gamma                97.183(6)
_cell_volume                     1323.97(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      26.2020
_cell_measurement_theta_min      2.4200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Nitromethane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13672
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         2.141
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00   60.00    --    0.00   0.00  45.00  180
  2  ω    -30.00  90.00   1.00   60.00    --    0.00  72.00  45.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       'ω 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                3762
_reflns_number_total             5051
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5051
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.058
_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)+(0.0697P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 F5A-F6A
 2.116 with sigma of 0.04
 F4B-F6B
 2.116 with sigma of 0.04
 F5B-F6B
 2.116 with sigma of 0.04
 F6A-F4A
 2.116 with sigma of 0.04
 F4A-F5A
 2.116 with sigma of 0.04
 F5B-F4B
 2.116 with sigma of 0.04
3. Rigid bond restraints
 F4B, F5A, F6B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F4A, F6A, F5B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(F4B)=Sof(F6B)=Sof(F5A)=1-FVAR(1)
 Sof(F4A)=Sof(F5B)=Sof(F6A)=FVAR(1)
5.a Free rotating group:
 O5(H5B,H5C)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2AB(H2AB), C3A(H3A), C2A(H2A), C5AB(H5AB), C6AB(H6AB), C3AB(H3AB),
 C5A(H5A), C6A(H6A)
5.c Idealised Me refined as rotating group:
 C8B(H8BA,H8BB,H8BC), C8(H8A,H8B,H8C), C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C)
5.d Idealised tetrahedral OH refined as rotating group:
 O3B(H3B)
;
_atom_sites_solution_hydrogens   mixed
_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
O3B O 0.43572(15) 0.28610(14) 0.38351(13) 0.0580(4) Uani 1 1 d . . . . .
H3B H 0.463479 0.229031 0.357900 0.087 Uiso 1 1 calc R U . . .
O3 O 0.53696(15) 0.11598(13) 0.32043(13) 0.0581(4) Uani 1 1 d . . . . .
O5 O 0.85435(16) 0.67113(15) 0.63779(17) 0.0717(5) Uani 1 1 d G . . . .
H5B H 0.823948 0.599081 0.623151 0.108 Uiso 1 1 d G U . . .
H5C H 0.783941 0.706059 0.613030 0.108 Uiso 1 1 d G U . . .
F2 F 0.89010(19) -0.09257(14) 0.81879(15) 0.0969(6) Uani 1 1 d . . . . .
N3 N 0.87692(18) 0.22183(14) 0.29897(14) 0.0494(4) Uani 1 1 d . . . . .
H3 H 0.965616 0.240229 0.324629 0.059 Uiso 1 1 calc R U . . .
F1 F 1.08257(19) 0.02094(16) 0.84551(15) 0.0982(6) Uani 1 1 d . . . . .
N1B N 0.53323(16) 0.33440(14) 0.47701(14) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.65840(17) 0.15794(14) 0.29113(14) 0.0470(4) Uani 1 1 d . . . . .
N3B N 0.72677(18) 0.43146(15) 0.57715(15) 0.0538(4) Uani 1 1 d . . . . .
F3 F 0.8994(3) 0.07899(18) 0.88746(14) 0.1182(8) Uani 1 1 d . . . . .
O4B O 0.30578(19) 0.21066(19) 0.56010(18) 0.0880(6) Uani 1 1 d . . . . .
C2 C 0.7847(2) 0.17194(16) 0.36015(17) 0.0456(4) Uani 1 1 d . . . . .
C5B C 0.5380(2) 0.30221(18) 0.58747(17) 0.0494(5) Uani 1 1 d . . . . .
C1A C 0.8216(2) 0.13632(17) 0.47651(17) 0.0464(5) Uani 1 1 d . . . . .
O4 O 0.5774(2) 0.2508(2) 0.00460(17) 0.1081(8) Uani 1 1 d . . . . .
C2B C 0.6479(2) 0.41016(17) 0.47231(17) 0.0480(5) Uani 1 1 d . . . . .
C4B C 0.6613(2) 0.36479(18) 0.64803(18) 0.0520(5) Uani 1 1 d . . . . .
F4B F 0.742(2) 0.5709(19) -0.0113(10) 0.167(7) Uani 0.46(2) 1 d D . P A 2
C1AB C 0.6840(2) 0.46117(17) 0.37015(18) 0.0493(5) Uani 1 1 d . . . . .
C5 C 0.6710(2) 0.19842(18) 0.18468(17) 0.0515(5) Uani 1 1 d . . . . .
C4 C 0.8100(2) 0.23876(18) 0.19163(17) 0.0514(5) Uani 1 1 d . . . . .
C4A C 0.9026(2) 0.05990(18) 0.69464(18) 0.0541(5) Uani 1 1 d . . . . .
F6B F 0.7853(18) 0.7273(11) 0.0800(12) 0.142(5) Uani 0.46(2) 1 d D . P A 2
C6B C 0.4220(2) 0.22734(19) 0.6214(2) 0.0581(5) Uani 1 1 d . . . . .
F5A F 0.9113(15) 0.5746(11) 0.0512(12) 0.130(5) Uani 0.46(2) 1 d D . P A 1
C2AB C 0.5858(2) 0.4694(2) 0.27122(19) 0.0581(5) Uani 1 1 d . . . . .
H2AB H 0.492059 0.440100 0.267609 0.070 Uiso 1 1 calc R U . . .
C4AB C 0.7645(3) 0.5632(2) 0.1823(2) 0.0589(5) Uani 1 1 d . . . . .
C3A C 0.7658(2) 0.0356(2) 0.6372(2) 0.0634(6) Uani 1 1 d . . . . .
H3A H 0.699897 -0.006710 0.671725 0.076 Uiso 1 1 calc R U . . .
C2A C 0.7242(2) 0.0727(2) 0.5297(2) 0.0603(6) Uani 1 1 d . . . . .
H2A H 0.630890 0.055394 0.492247 0.072 Uiso 1 1 calc R U . . .
C1 C 0.9437(3) 0.0181(2) 0.8108(2) 0.0691(6) Uani 1 1 d . . . . .
C5AB C 0.8633(3) 0.5573(2) 0.2804(2) 0.0681(6) Uani 1 1 d . . . . .
H5AB H 0.956656 0.587617 0.283809 0.082 Uiso 1 1 calc R U . . .
C8B C 0.7253(3) 0.3701(3) 0.7713(2) 0.0718(7) Uani 1 1 d . . . . .
H8BA H 0.769570 0.301388 0.789247 0.108 Uiso 1 1 calc R U . . .
H8BB H 0.653459 0.374207 0.814540 0.108 Uiso 1 1 calc R U . . .
H8BC H 0.794268 0.438072 0.789445 0.108 Uiso 1 1 calc R U . . .
C6 C 0.5562(3) 0.1936(2) 0.0844(2) 0.0679(6) Uani 1 1 d . . . . .
C6AB C 0.8232(2) 0.5064(2) 0.3733(2) 0.0635(6) Uani 1 1 d . . . . .
H6AB H 0.890208 0.502257 0.439058 0.076 Uiso 1 1 calc R U . . .
C3AB C 0.6258(3) 0.5205(2) 0.1782(2) 0.0620(6) Uani 1 1 d . . . . .
H3AB H 0.559006 0.526021 0.112568 0.074 Uiso 1 1 calc R U . . .
C5A C 0.9994(3) 0.1230(2) 0.6430(2) 0.0737(7) Uani 1 1 d . . . . .
H5A H 1.092477 0.140002 0.681096 0.088 Uiso 1 1 calc R U . . .
C6A C 0.9595(2) 0.1611(2) 0.5356(2) 0.0699(7) Uani 1 1 d . . . . .
H6A H 1.025928 0.204043 0.502024 0.084 Uiso 1 1 calc R U . . .
C8 C 0.8874(3) 0.2890(2) 0.1056(2) 0.0665(6) Uani 1 1 d . . . . .
H8A H 0.981950 0.319156 0.142027 0.100 Uiso 1 1 calc R U . . .
H8B H 0.841143 0.351069 0.070085 0.100 Uiso 1 1 calc R U . . .
H8C H 0.889173 0.229346 0.049356 0.100 Uiso 1 1 calc R U . . .
C1B C 0.8088(3) 0.6194(3) 0.0814(2) 0.0761(7) Uani 1 1 d . . . . .
C7B C 0.4482(3) 0.1735(2) 0.7330(2) 0.0762(7) Uani 1 1 d . . . . .
H7BA H 0.445873 0.230278 0.791780 0.114 Uiso 1 1 calc R U . . .
H7BB H 0.538738 0.146780 0.745825 0.114 Uiso 1 1 calc R U . . .
H7BC H 0.376879 0.108533 0.733468 0.114 Uiso 1 1 calc R U . . .
C7 C 0.4197(3) 0.1201(3) 0.0806(3) 0.1003(11) Uani 1 1 d . . . . .
H7A H 0.367033 0.156820 0.127310 0.150 Uiso 1 1 calc R U . . .
H7B H 0.436327 0.044770 0.108187 0.150 Uiso 1 1 calc R U . . .
H7C H 0.367545 0.111006 0.003880 0.150 Uiso 1 1 calc R U . . .
F4A F 0.7111(12) 0.5997(13) -0.0136(9) 0.124(4) Uani 0.54(2) 1 d D . P A 1
F5B F 0.9412(12) 0.6203(17) 0.0812(12) 0.166(6) Uani 0.54(2) 1 d D . P A 2
F6A F 0.8405(18) 0.7299(7) 0.0916(8) 0.130(4) Uani 0.54(2) 1 d D . 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
O3B H3B 0.8200 . ?
O3B N1B 1.380(2) . ?
O3 N1 1.343(2) . ?
O5 H5B 0.8505 . ?
O5 H5C 0.8492 . ?
F2 C1 1.334(3) . ?
N3 H3 0.8600 . ?
N3 C2 1.358(3) . ?
N3 C4 1.360(3) . ?
F1 C1 1.337(3) . ?
N1B C5B 1.384(3) . ?
N1B C2B 1.346(3) . ?
N1 C2 1.336(3) . ?
N1 C5 1.398(3) . ?
N3B C2B 1.343(3) . ?
N3B C4B 1.363(3) . ?
F3 C1 1.319(3) . ?
O4B C6B 1.218(3) . ?
C2 C1A 1.459(3) . ?
C5B C4B 1.387(3) . ?
C5B C6B 1.469(3) . ?
C1A C2A 1.396(3) . ?
C1A C6A 1.388(3) . ?
O4 C6 1.215(3) . ?
C2B C1AB 1.463(3) . ?
C4B C8B 1.490(3) . ?
F4B C1B 1.258(12) . ?
C1AB C2AB 1.388(3) . ?
C1AB C6AB 1.390(3) . ?
C5 C4 1.368(3) . ?
C5 C6 1.474(3) . ?
C4 C8 1.488(3) . ?
C4A C3A 1.372(3) . ?
C4A C1 1.486(3) . ?
C4A C5A 1.378(3) . ?
F6B C1B 1.296(11) . ?
C6B C7B 1.484(4) . ?
F5A C1B 1.293(10) . ?
C2AB H2AB 0.9300 . ?
C2AB C3AB 1.381(3) . ?
C4AB C5AB 1.380(3) . ?
C4AB C3AB 1.376(3) . ?
C4AB C1B 1.504(4) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.374(3) . ?
C2A H2A 0.9300 . ?
C5AB H5AB 0.9300 . ?
C5AB C6AB 1.378(4) . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C6 C7 1.483(4) . ?
C6AB H6AB 0.9300 . ?
C3AB H3AB 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.375(3) . ?
C6A H6A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C1B F4A 1.333(10) . ?
C1B F5B 1.296(10) . ?
C1B F6A 1.273(8) . ?
C7B H7BA 0.9600 . ?
C7B H7BB 0.9600 . ?
C7B H7BC 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1B O3B H3B 109.5 . . ?
H5B O5 H5C 104.5 . . ?
C2 N3 H3 124.6 . . ?
C2 N3 C4 110.79(17) . . ?
C4 N3 H3 124.6 . . ?
O3B N1B C5B 125.46(17) . . ?
C2B N1B O3B 124.52(17) . . ?
C2B N1B C5B 109.59(16) . . ?
O3 N1 C5 125.02(17) . . ?
C2 N1 O3 125.41(17) . . ?
C2 N1 C5 109.52(17) . . ?
C2B N3B C4B 107.00(17) . . ?
N3 C2 C1A 125.40(18) . . ?
N1 C2 N3 106.43(18) . . ?
N1 C2 C1A 128.09(18) . . ?
N1B C5B C4B 104.15(18) . . ?
N1B C5B C6B 122.43(19) . . ?
C4B C5B C6B 133.1(2) . . ?
C2A C1A C2 122.33(18) . . ?
C6A C1A C2 119.47(18) . . ?
C6A C1A C2A 118.1(2) . . ?
N1B C2B C1AB 126.23(18) . . ?
N3B C2B N1B 109.21(18) . . ?
N3B C2B C1AB 124.56(18) . . ?
N3B C4B C5B 110.02(18) . . ?
N3B C4B C8B 119.25(19) . . ?
C5B C4B C8B 130.7(2) . . ?
C2AB C1AB C2B 123.40(19) . . ?
C2AB C1AB C6AB 118.3(2) . . ?
C6AB C1AB C2B 118.25(19) . . ?
N1 C5 C6 125.9(2) . . ?
C4 C5 N1 106.64(18) . . ?
C4 C5 C6 127.4(2) . . ?
N3 C4 C5 106.61(18) . . ?
N3 C4 C8 121.8(2) . . ?
C5 C4 C8 131.5(2) . . ?
C3A C4A C1 119.7(2) . . ?
C3A C4A C5A 119.0(2) . . ?
C5A C4A C1 121.3(2) . . ?
O4B C6B C5B 121.0(2) . . ?
O4B C6B C7B 120.3(2) . . ?
C5B C6B C7B 118.8(2) . . ?
C1AB C2AB H2AB 119.6 . . ?
C3AB C2AB C1AB 120.7(2) . . ?
C3AB C2AB H2AB 119.6 . . ?
C5AB C4AB C1B 119.6(2) . . ?
C3AB C4AB C5AB 120.0(2) . . ?
C3AB C4AB C1B 120.4(2) . . ?
C4A C3A H3A 119.4 . . ?
C4A C3A C2A 121.3(2) . . ?
C2A C3A H3A 119.4 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.2(2) . . ?
C3A C2A H2A 119.9 . . ?
F2 C1 F1 105.1(2) . . ?
F2 C1 C4A 112.4(2) . . ?
F1 C1 C4A 113.5(2) . . ?
F3 C1 F2 105.7(2) . . ?
F3 C1 F1 107.1(2) . . ?
F3 C1 C4A 112.5(2) . . ?
C4AB C5AB H5AB 120.1 . . ?
C6AB C5AB C4AB 119.8(2) . . ?
C6AB C5AB H5AB 120.1 . . ?
C4B C8B H8BA 109.5 . . ?
C4B C8B H8BB 109.5 . . ?
C4B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O4 C6 C5 117.9(2) . . ?
O4 C6 C7 121.2(2) . . ?
C5 C6 C7 120.9(2) . . ?
C1AB C6AB H6AB 119.5 . . ?
C5AB C6AB C1AB 121.0(2) . . ?
C5AB C6AB H6AB 119.5 . . ?
C2AB C3AB H3AB 120.0 . . ?
C4AB C3AB C2AB 120.1(2) . . ?
C4AB C3AB H3AB 120.0 . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A C4A 120.5(2) . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A C1A 120.9(2) . . ?
C5A C6A H6A 119.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F4B C1B F6B 106.6(10) . . ?
F4B C1B C4AB 112.7(8) . . ?
F4B C1B F5B 107.0(15) . . ?
F6B C1B C4AB 109.9(7) . . ?
F6B C1B F5B 106.7(13) . . ?
F5A C1B C4AB 112.7(6) . . ?
F5A C1B F4A 100.6(10) . . ?
F4A C1B C4AB 113.5(6) . . ?
F5B C1B C4AB 113.5(5) . . ?
F6A C1B F5A 108.6(11) . . ?
F6A C1B C4AB 115.3(5) . . ?
F6A C1B F4A 105.0(8) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
_geom_hbond_publ_flag
O3B H3B O3 0.82 1.66 2.478(2) 172.6 . yes
O5 H5B N3B 0.85 2.06 2.906(2) 172.7 . yes
O5 H5C O3B 0.85 2.17 2.906(2) 144.5 2_666 yes
N3 H3 O5 0.86 1.89 2.717(2) 160.8 2_766 yes
C2A H2A O3 0.93 2.26 2.903(3) 125.9 . yes

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
O3B N1B C5B C4B 173.48(17) . . . . ?
O3B N1B C5B C6B -12.2(3) . . . . ?
O3B N1B C2B N3B -174.34(16) . . . . ?
O3B N1B C2B C1AB 4.9(3) . . . . ?
O3 N1 C2 N3 -176.90(16) . . . . ?
O3 N1 C2 C1A 6.0(3) . . . . ?
O3 N1 C5 C4 176.94(17) . . . . ?
O3 N1 C5 C6 -5.1(3) . . . . ?
N3 C2 C1A C2A -172.00(19) . . . . ?
N3 C2 C1A C6A 4.8(3) . . . . ?
N1B C5B C4B N3B 0.2(2) . . . . ?
N1B C5B C4B C8B 178.9(2) . . . . ?
N1B C5B C6B O4B -15.8(3) . . . . ?
N1B C5B C6B C7B 165.2(2) . . . . ?
N1B C2B C1AB C2AB 22.1(3) . . . . ?
N1B C2B C1AB C6AB -159.6(2) . . . . ?
N1 C2 C1A C2A 4.5(3) . . . . ?
N1 C2 C1A C6A -178.6(2) . . . . ?
N1 C5 C4 N3 0.3(2) . . . . ?
N1 C5 C4 C8 178.3(2) . . . . ?
N1 C5 C6 O4 166.8(2) . . . . ?
N1 C5 C6 C7 -13.9(4) . . . . ?
N3B C2B C1AB C2AB -158.8(2) . . . . ?
N3B C2B C1AB C6AB 19.6(3) . . . . ?
C2 N3 C4 C5 0.1(2) . . . . ?
C2 N3 C4 C8 -178.18(19) . . . . ?
C2 N1 C5 C4 -0.5(2) . . . . ?
C2 N1 C5 C6 177.4(2) . . . . ?
C2 C1A C2A C3A 176.4(2) . . . . ?
C2 C1A C6A C5A -176.3(2) . . . . ?
C5B N1B C2B N3B -1.6(2) . . . . ?
C5B N1B C2B C1AB 177.70(18) . . . . ?
C2B N1B C5B C4B 0.8(2) . . . . ?
C2B N1B C5B C6B 175.11(18) . . . . ?
C2B N3B C4B C5B -1.2(2) . . . . ?
C2B N3B C4B C8B 179.94(19) . . . . ?
C2B C1AB C2AB C3AB 178.8(2) . . . . ?
C2B C1AB C6AB C5AB -178.9(2) . . . . ?
C4B N3B C2B N1B 1.7(2) . . . . ?
C4B N3B C2B C1AB -177.62(18) . . . . ?
C4B C5B C6B O4B 156.6(2) . . . . ?
C4B C5B C6B C7B -22.4(4) . . . . ?
C1AB C2AB C3AB C4AB 0.5(3) . . . . ?
C5 N1 C2 N3 0.6(2) . . . . ?
C5 N1 C2 C1A -176.49(18) . . . . ?
C4 N3 C2 N1 -0.4(2) . . . . ?
C4 N3 C2 C1A 176.77(18) . . . . ?
C4 C5 C6 O4 -15.6(4) . . . . ?
C4 C5 C6 C7 163.6(3) . . . . ?
C4A C3A C2A C1A 0.0(4) . . . . ?
C4A C5A C6A C1A -0.4(4) . . . . ?
C6B C5B C4B N3B -173.2(2) . . . . ?
C6B C5B C4B C8B 5.6(4) . . . . ?
C2AB C1AB C6AB C5AB -0.5(3) . . . . ?
C4AB C5AB C6AB C1AB -0.4(4) . . . . ?
C3A C4A C1 F2 44.9(3) . . . . ?
C3A C4A C1 F1 164.0(2) . . . . ?
C3A C4A C1 F3 -74.3(3) . . . . ?
C3A C4A C5A C6A 0.0(4) . . . . ?
C2A C1A C6A C5A 0.7(4) . . . . ?
C1 C4A C3A C2A -179.9(2) . . . . ?
C1 C4A C5A C6A -179.9(2) . . . . ?
C5AB C4AB C3AB C2AB -1.4(3) . . . . ?
C5AB C4AB C1B F4B 145.1(13) . . . . ?
C5AB C4AB C1B F6B -96.1(9) . . . . ?
C5AB C4AB C1B F5A 54.3(8) . . . . ?
C5AB C4AB C1B F4A 167.7(7) . . . . ?
C5AB C4AB C1B F5B 23.3(11) . . . . ?
C5AB C4AB C1B F6A -71.2(9) . . . . ?
C6 C5 C4 N3 -177.6(2) . . . . ?
C6 C5 C4 C8 0.4(4) . . . . ?
C6AB C1AB C2AB C3AB 0.4(3) . . . . ?
C3AB C4AB C5AB C6AB 1.3(4) . . . . ?
C3AB C4AB C1B F4B -36.5(14) . . . . ?
C3AB C4AB C1B F6B 82.2(9) . . . . ?
C3AB C4AB C1B F5A -127.4(8) . . . . ?
C3AB C4AB C1B F4A -13.9(8) . . . . ?
C3AB C4AB C1B F5B -158.4(11) . . . . ?
C3AB C4AB C1B F6A 107.2(9) . . . . ?
C5A C4A C3A C2A 0.2(4) . . . . ?
C5A C4A C1 F2 -135.2(3) . . . . ?
C5A C4A C1 F1 -16.1(3) . . . . ?
C5A C4A C1 F3 105.6(3) . . . . ?
C6A C1A C2A C3A -0.5(3) . . . . ?
C1B C4AB C5AB C6AB 179.7(2) . . . . ?
C1B C4AB C3AB C2AB -179.8(2) . . . . ?

_olex2_submission_original_sample_id PANI-114_CH3NO2
_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
;
####################################################################### 
# 
# 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_4b_pani116_ch3coch3
_database_code_depnum_ccdc_archive 'CCDC 2340435'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
4-(5-acetyl-1-hydroxy-4-methyl-1H-imidazol-2-yl)benzonitrile
_chemical_formula_moiety         'C13 H11 N3 O2'
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6508(11)
_cell_length_b                   6.9360(8)
_cell_length_c                   12.6244(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.350(8)
_cell_angle_gamma                90
_cell_volume                     1193.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2551
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0470
_cell_measurement_theta_min      3.2410
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51656
_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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_preparation       'chemical synthesis'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12229
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.141
_diffrn_reflns_theta_min         3.233
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00   60.00    --    0.00   0.00  45.00  180
  2  ω    -30.00  90.00   1.00   60.00    --    0.00  72.00  45.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       'ω 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                1729
_reflns_number_total             2501
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.045
_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)+(0.0734P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1411
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C6A(H6A), C3A(H3A), C5A(H5A)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O3 O 0.38408(9) 0.6213(2) 0.43023(9) 0.0661(4) Uani 1 1 d . . . . .
H3 H 0.341369 0.619897 0.473279 0.099 Uiso 1 1 calc R U . . .
N1 N 0.34153(10) 0.59799(19) 0.32940(11) 0.0466(4) Uani 1 1 d . . . . .
N3 N 0.32328(10) 0.5735(2) 0.15687(11) 0.0516(4) Uani 1 1 d . . . . .
O4 O 0.20755(11) 0.5851(3) 0.48320(11) 0.0868(5) Uani 1 1 d . . . . .
C2 C 0.38873(11) 0.5924(2) 0.24000(13) 0.0434(4) Uani 1 1 d . . . . .
C1A C 0.49513(11) 0.5998(2) 0.22965(13) 0.0439(4) Uani 1 1 d . . . . .
C5 C 0.24121(11) 0.5838(2) 0.30584(13) 0.0481(4) Uani 1 1 d . . . . .
C4 C 0.23357(11) 0.5674(2) 0.19626(14) 0.0507(4) Uani 1 1 d . . . . .
C2A C 0.56384(12) 0.5876(2) 0.31534(14) 0.0533(4) Uani 1 1 d . . . . .
H2A H 0.543097 0.580696 0.384107 0.064 Uiso 1 1 calc R U . . .
C6A C 0.52783(12) 0.6133(2) 0.12813(14) 0.0536(4) Uani 1 1 d . . . . .
H6A H 0.482301 0.624676 0.070736 0.064 Uiso 1 1 calc R U . . .
C4A C 0.69422(12) 0.5952(2) 0.19666(15) 0.0517(4) Uani 1 1 d . . . . .
C3A C 0.66278(12) 0.5857(3) 0.29811(15) 0.0566(5) Uani 1 1 d . . . . .
H3A H 0.708522 0.578012 0.355511 0.068 Uiso 1 1 calc R U . . .
N2 N 0.87994(13) 0.5844(3) 0.16566(18) 0.0871(6) Uani 1 1 d . . . . .
C5A C 0.62668(12) 0.6101(3) 0.11042(15) 0.0580(5) Uani 1 1 d . . . . .
H5A H 0.647710 0.617898 0.041800 0.070 Uiso 1 1 calc R U . . .
C6 C 0.17449(13) 0.5823(3) 0.38976(15) 0.0597(5) Uani 1 1 d . . . . .
C1 C 0.79821(13) 0.5892(3) 0.17896(16) 0.0634(5) Uani 1 1 d . . . . .
C7 C 0.06660(14) 0.5798(3) 0.36489(18) 0.0769(6) Uani 1 1 d . . . . .
H7A H 0.049633 0.676172 0.312414 0.115 Uiso 1 1 calc R U . . .
H7B H 0.033284 0.606423 0.428173 0.115 Uiso 1 1 calc R U . . .
H7C H 0.047270 0.455126 0.338048 0.115 Uiso 1 1 calc R U . . .
C13 C 0.14387(14) 0.5377(4) 0.12394(16) 0.0799(7) Uani 1 1 d . . . . .
H13A H 0.162516 0.528795 0.051945 0.120 Uiso 1 1 calc R U . . .
H13B H 0.099939 0.644516 0.130544 0.120 Uiso 1 1 calc R U . . .
H13C H 0.111684 0.420686 0.142974 0.120 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
O3 H3 0.8200 . ?
O3 N1 1.3775(17) . ?
N1 C2 1.332(2) . ?
N1 C5 1.388(2) . ?
N3 C2 1.344(2) . ?
N3 C4 1.349(2) . ?
O4 C6 1.238(2) . ?
C2 C1A 1.467(2) . ?
C1A C2A 1.392(2) . ?
C1A C6A 1.385(3) . ?
C5 C4 1.386(3) . ?
C5 C6 1.437(3) . ?
C4 C13 1.498(2) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.381(2) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.381(2) . ?
C4A C3A 1.376(3) . ?
C4A C5A 1.389(2) . ?
C4A C1 1.450(2) . ?
C3A H3A 0.9300 . ?
N2 C1 1.138(3) . ?
C5A H5A 0.9300 . ?
C6 C7 1.488(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O3 H3 109.5 . . ?
O3 N1 C5 124.32(14) . . ?
C2 N1 O3 125.98(14) . . ?
C2 N1 C5 109.66(13) . . ?
C2 N3 C4 106.95(14) . . ?
N1 C2 N3 109.38(14) . . ?
N1 C2 C1A 127.21(14) . . ?
N3 C2 C1A 123.39(15) . . ?
C2A C1A C2 123.65(16) . . ?
C6A C1A C2 117.34(14) . . ?
C6A C1A C2A 118.97(16) . . ?
N1 C5 C6 120.17(15) . . ?
C4 C5 N1 103.62(14) . . ?
C4 C5 C6 136.16(16) . . ?
N3 C4 C5 110.39(14) . . ?
N3 C4 C13 120.45(16) . . ?
C5 C4 C13 129.11(16) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 119.93(17) . . ?
C3A C2A H2A 120.0 . . ?
C1A C6A H6A 119.3 . . ?
C5A C6A C1A 121.31(16) . . ?
C5A C6A H6A 119.3 . . ?
C3A C4A C5A 120.30(16) . . ?
C3A C4A C1 120.22(16) . . ?
C5A C4A C1 119.48(17) . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.49(16) . . ?
C4A C3A H3A 119.8 . . ?
C6A C5A C4A 118.98(17) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
O4 C6 C5 119.39(17) . . ?
O4 C6 C7 120.16(17) . . ?
C5 C6 C7 120.45(17) . . ?
N2 C1 C4A 179.6(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
_geom_hbond_publ_flag
O3 H3 O4 0.82 1.85 2.5506(19) 142.0 . yes
C2A H2A O3 0.93 2.30 2.932(2) 125.0 . yes

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
O3 N1 C2 N3 -178.23(13) . . . . ?
O3 N1 C2 C1A 3.3(2) . . . . ?
O3 N1 C5 C4 178.49(14) . . . . ?
O3 N1 C5 C6 -3.5(2) . . . . ?
N1 C2 C1A C2A 9.2(2) . . . . ?
N1 C2 C1A C6A -173.04(15) . . . . ?
N1 C5 C4 N3 -0.62(18) . . . . ?
N1 C5 C4 C13 176.70(19) . . . . ?
N1 C5 C6 O4 -3.2(3) . . . . ?
N1 C5 C6 C7 176.06(17) . . . . ?
N3 C2 C1A C2A -169.09(15) . . . . ?
N3 C2 C1A C6A 8.7(2) . . . . ?
C2 N1 C5 C4 0.61(17) . . . . ?
C2 N1 C5 C6 178.66(15) . . . . ?
C2 N3 C4 C5 0.41(19) . . . . ?
C2 N3 C4 C13 -177.18(17) . . . . ?
C2 C1A C2A C3A 176.63(15) . . . . ?
C2 C1A C6A C5A -176.30(16) . . . . ?
C1A C2A C3A C4A -0.2(3) . . . . ?
C1A C6A C5A C4A -0.7(3) . . . . ?
C5 N1 C2 N3 -0.40(17) . . . . ?
C5 N1 C2 C1A -178.88(15) . . . . ?
C4 N3 C2 N1 0.00(17) . . . . ?
C4 N3 C2 C1A 178.55(14) . . . . ?
C4 C5 C6 O4 174.0(2) . . . . ?
C4 C5 C6 C7 -6.7(3) . . . . ?
C2A C1A C6A C5A 1.6(2) . . . . ?
C6A C1A C2A C3A -1.1(2) . . . . ?
C3A C4A C5A C6A -0.7(3) . . . . ?
C5A C4A C3A C2A 1.1(3) . . . . ?
C6 C5 C4 N3 -178.18(19) . . . . ?
C6 C5 C4 C13 -0.9(3) . . . . ?
C1 C4A C3A C2A -178.75(16) . . . . ?
C1 C4A C5A C6A 179.21(16) . . . . ?

_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
;
####################################################################### 
# 
# 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_3b_pani164_etoh
_database_code_depnum_ccdc_archive 'CCDC 2340467'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
'2-(4-cyanophenyl)-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-benzo[d]imidazole 3-oxide'
_chemical_formula_moiety         'C16 H15 N3 O2'
_chemical_formula_sum            'C16 H15 N3 O2'
_chemical_formula_weight         281.31
_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'

_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                   5.7707(9)
_cell_length_b                   24.525(3)
_cell_length_c                   10.1461(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.696(17)
_cell_angle_gamma                90
_cell_volume                     1432.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    298(4)
_cell_measurement_theta_max      27.6550
_cell_measurement_theta_min      3.2140
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'chemical synthesis'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.228
_diffrn_reflns_theta_min         2.176
_diffrn_ambient_temperature      298(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  90.00   1.00  120.00    --    0.00   0.00  45.00  180
  2  ω    -90.00  30.00   1.00  120.00    --    0.00 -72.00 225.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Tongda TD-5000'
_diffrn_measurement_method       'ω 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                1807
_reflns_number_total             3107
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.041
_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)+(0.0661P)²+0.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1615
_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
 H3-N3
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C5(H5B,H5C), C7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C6A(H6A), C3A(H3A), C5A(H5A)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8075(3) 0.73826(7) 0.49640(17) 0.0426(5) Uani 1 1 d . . . . .
O1 O 0.8638(3) 0.70569(7) 0.59971(16) 0.0616(5) Uani 1 1 d . . . . .
N3 N 0.6211(3) 0.77302(7) 0.32200(19) 0.0451(5) Uani 1 1 d D . . . .
H3 H 0.512(4) 0.7784(9) 0.250(2) 0.054 Uiso 1 1 d D U . . .
O2 O 1.2555(3) 0.79022(8) 0.6099(2) 0.0752(6) Uani 1 1 d . . . . .
C2 C 0.6309(4) 0.72966(8) 0.4066(2) 0.0412(5) Uani 1 1 d . . . . .
C4 C 0.7952(4) 0.80782(9) 0.3566(2) 0.0437(6) Uani 1 1 d . . . . .
C9 C 0.9152(4) 0.78710(9) 0.4668(2) 0.0434(6) Uani 1 1 d . . . . .
C1A C 0.4752(4) 0.68257(9) 0.3945(2) 0.0413(5) Uani 1 1 d . . . . .
C2A C 0.5379(4) 0.63249(9) 0.4500(2) 0.0480(6) Uani 1 1 d . . . . .
H2A H 0.679469 0.628845 0.498491 0.058 Uiso 1 1 calc R U . . .
C8 C 1.1298(4) 0.81071(10) 0.5216(2) 0.0506(6) Uani 1 1 d . . . . .
C6A C 0.2628(4) 0.68704(9) 0.3208(2) 0.0491(6) Uani 1 1 d . . . . .
H6A H 0.219807 0.720220 0.282228 0.059 Uiso 1 1 calc R U . . .
C4A C 0.1799(4) 0.59311(9) 0.3627(2) 0.0508(6) Uani 1 1 d . . . . .
C3A C 0.3913(4) 0.58793(9) 0.4338(3) 0.0546(7) Uani 1 1 d . . . . .
H3A H 0.435085 0.554488 0.470697 0.066 Uiso 1 1 calc R U . . .
C6 C 1.0064(4) 0.89593(9) 0.3807(2) 0.0496(6) Uani 1 1 d . . . . .
C5A C 0.1167(4) 0.64278(10) 0.3048(2) 0.0534(7) Uani 1 1 d . . . . .
H5A H -0.024005 0.646115 0.255414 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8572(5) 0.85866(9) 0.2866(3) 0.0563(7) Uani 1 1 d . . . . .
H5B H 0.716770 0.877710 0.255632 0.068 Uiso 1 1 calc R U . . .
H5C H 0.942958 0.849517 0.210515 0.068 Uiso 1 1 calc R U . . .
C7 C 1.2005(4) 0.86191(10) 0.4508(3) 0.0569(7) Uani 1 1 d . . . . .
H7A H 1.308354 0.851502 0.385792 0.068 Uiso 1 1 calc R U . . .
H7B H 1.284375 0.885180 0.514843 0.068 Uiso 1 1 calc R U . . .
C1 C 0.0240(5) 0.54713(12) 0.3455(3) 0.0694(8) Uani 1 1 d . . . . .
C11 C 1.1193(5) 0.94043(10) 0.2993(3) 0.0680(8) Uani 1 1 d . . . . .
H11A H 1.211113 0.923672 0.234846 0.102 Uiso 1 1 calc R U . . .
H11B H 1.216918 0.962944 0.356925 0.102 Uiso 1 1 calc R U . . .
H11C H 1.000432 0.962436 0.255317 0.102 Uiso 1 1 calc R U . . .
N2 N -0.0994(5) 0.51124(12) 0.3317(4) 0.1071(11) Uani 1 1 d . . . . .
C10 C 0.8546(5) 0.92210(11) 0.4813(3) 0.0732(9) Uani 1 1 d . . . . .
H10A H 0.742540 0.945676 0.436423 0.110 Uiso 1 1 calc R U . . .
H10B H 0.950332 0.942943 0.543642 0.110 Uiso 1 1 calc R U . . .
H10C H 0.775532 0.894122 0.527040 0.110 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
N1 O1 1.341(2) . ?
N1 C2 1.339(3) . ?
N1 C9 1.391(3) . ?
N3 H3 0.942(16) . ?
N3 C2 1.365(3) . ?
N3 C4 1.348(3) . ?
O2 C8 1.224(3) . ?
C2 C1A 1.463(3) . ?
C4 C9 1.374(3) . ?
C4 C5 1.490(3) . ?
C9 C8 1.446(3) . ?
C1A C2A 1.389(3) . ?
C1A C6A 1.398(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.386(3) . ?
C8 C7 1.515(3) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.378(3) . ?
C4A C3A 1.382(3) . ?
C4A C5A 1.391(3) . ?
C4A C1 1.446(4) . ?
C3A H3A 0.9300 . ?
C6 C5 1.543(3) . ?
C6 C7 1.535(3) . ?
C6 C11 1.538(3) . ?
C6 C10 1.529(4) . ?
C5A H5A 0.9300 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 N2 1.135(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C9 126.35(17) . . ?
C2 N1 O1 124.99(18) . . ?
C2 N1 C9 108.63(17) . . ?
C2 N3 H3 126.6(15) . . ?
C4 N3 H3 124.2(14) . . ?
C4 N3 C2 109.24(18) . . ?
N1 C2 N3 107.69(18) . . ?
N1 C2 C1A 128.10(19) . . ?
N3 C2 C1A 124.19(18) . . ?
N3 C4 C9 107.8(2) . . ?
N3 C4 C5 127.14(19) . . ?
C9 C4 C5 125.0(2) . . ?
N1 C9 C8 130.2(2) . . ?
C4 C9 N1 106.59(18) . . ?
C4 C9 C8 122.6(2) . . ?
C2A C1A C2 121.42(19) . . ?
C2A C1A C6A 118.9(2) . . ?
C6A C1A C2 119.66(19) . . ?
C1A C2A H2A 119.7 . . ?
C3A C2A C1A 120.5(2) . . ?
C3A C2A H2A 119.7 . . ?
O2 C8 C9 124.7(2) . . ?
O2 C8 C7 121.5(2) . . ?
C9 C8 C7 113.6(2) . . ?
C1A C6A H6A 119.7 . . ?
C5A C6A C1A 120.7(2) . . ?
C5A C6A H6A 119.7 . . ?
C3A C4A C5A 120.0(2) . . ?
C3A C4A C1 120.8(2) . . ?
C5A C4A C1 119.2(2) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A C2A 120.1(2) . . ?
C4A C3A H3A 120.0 . . ?
C7 C6 C5 109.05(19) . . ?
C7 C6 C11 108.2(2) . . ?
C11 C6 C5 109.1(2) . . ?
C10 C6 C5 109.9(2) . . ?
C10 C6 C7 110.5(2) . . ?
C10 C6 C11 110.0(2) . . ?
C6A C5A C4A 119.9(2) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
C4 C5 C6 110.03(19) . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 H5C 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C6 C5 H5C 109.7 . . ?
H5B C5 H5C 108.2 . . ?
C8 C7 C6 117.35(19) . . ?
C8 C7 H7A 108.0 . . ?
C8 C7 H7B 108.0 . . ?
C6 C7 H7A 108.0 . . ?
C6 C7 H7B 108.0 . . ?
H7A C7 H7B 107.2 . . ?
N2 C1 C4A 179.6(4) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
_geom_hbond_publ_flag
N3 H3 O1 0.942(16) 1.744(17) 2.671(2) 167(2) 4_575 yes
C2A H2A O1 0.93 2.37 2.949(3) 120.5 . yes

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
N1 C2 C1A C2A -21.4(4) . . . . ?
N1 C2 C1A C6A 161.5(2) . . . . ?
N1 C9 C8 O2 -1.3(4) . . . . ?
N1 C9 C8 C7 173.4(2) . . . . ?
O1 N1 C2 N3 176.5(2) . . . . ?
O1 N1 C2 C1A -4.9(4) . . . . ?
O1 N1 C9 C4 -177.3(2) . . . . ?
O1 N1 C9 C8 11.5(4) . . . . ?
N3 C2 C1A C2A 156.9(2) . . . . ?
N3 C2 C1A C6A -20.2(4) . . . . ?
N3 C4 C9 N1 0.5(3) . . . . ?
N3 C4 C9 C8 172.5(2) . . . . ?
N3 C4 C5 C6 160.6(2) . . . . ?
O2 C8 C7 C6 -158.2(3) . . . . ?
C2 N1 C9 C4 0.6(3) . . . . ?
C2 N1 C9 C8 -170.6(2) . . . . ?
C2 N3 C4 C9 -1.4(3) . . . . ?
C2 N3 C4 C5 176.2(2) . . . . ?
C2 C1A C2A C3A -177.8(2) . . . . ?
C2 C1A C6A C5A 178.0(2) . . . . ?
C4 N3 C2 N1 1.8(3) . . . . ?
C4 N3 C2 C1A -176.9(2) . . . . ?
C4 C9 C8 O2 -171.4(3) . . . . ?
C4 C9 C8 C7 3.3(3) . . . . ?
C9 N1 C2 N3 -1.5(3) . . . . ?
C9 N1 C2 C1A 177.1(2) . . . . ?
C9 C4 C5 C6 -22.3(4) . . . . ?
C9 C8 C7 C6 26.9(3) . . . . ?
C1A C2A C3A C4A -0.5(4) . . . . ?
C1A C6A C5A C4A 0.2(4) . . . . ?
C2A C1A C6A C5A 0.8(4) . . . . ?
C6A C1A C2A C3A -0.7(4) . . . . ?
C3A C4A C5A C6A -1.4(4) . . . . ?
C5A C4A C3A C2A 1.5(4) . . . . ?
C5 C4 C9 N1 -177.2(2) . . . . ?
C5 C4 C9 C8 -5.1(4) . . . . ?
C5 C6 C7 C8 -53.1(3) . . . . ?
C7 C6 C5 C4 47.7(3) . . . . ?
C1 C4A C3A C2A -179.5(3) . . . . ?
C1 C4A C5A C6A 179.7(2) . . . . ?
C11 C6 C5 C4 165.7(2) . . . . ?
C11 C6 C7 C8 -171.6(2) . . . . ?
C10 C6 C5 C4 -73.6(3) . . . . ?
C10 C6 C7 C8 67.9(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_10b_pani189_etoh
_database_code_depnum_ccdc_archive 'CCDC 2340466'
loop_
_audit_author_name
_audit_author_address
'Sergey Arkhipov'
;Novosibirsk State University
Russia
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-06-26 downloaded from the CCDC.
;
_audit_creation_date             2024-03-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
3-((2-bromobenzyl)oxy)-6,6-dimethyl-2-(4-nitrophenyl)-3,5,6,7-tetrahydro-4H-benzo[d]imidazol-4-one
_chemical_formula_moiety         'C22 H20 Br N3 O4'
_chemical_formula_sum            'C22 H20 Br N3 O4'
_chemical_formula_weight         470.32
_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'
Br Br -0.2901 2.4595 '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                   9.339(2)
_cell_length_b                   13.222(2)
_cell_length_c                   18.311(4)
_cell_angle_alpha                78.539(16)
_cell_angle_beta                 77.793(19)
_cell_angle_gamma                77.049(17)
_cell_volume                     2126.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    295(4)
_cell_measurement_theta_max      26.2660
_cell_measurement_theta_min      2.7240
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.694
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_preparation       'chemical synthesis'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.1519
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16882
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.116
_diffrn_ambient_temperature      295(4)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  30.00   1.00  120.00    --    0.00   0.00  45.00  120
  2  ω    -90.00  30.00   1.00  120.00    --    0.00 -72.00 225.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω 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                3046
_reflns_number_total             7829
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2227
_refine_ls_R_factor_gt           0.0895
_refine_ls_restrained_S_all      1.018
_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)+(0.1333P)²+1.0369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2353
_refine_ls_wR_factor_ref         0.2957
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C13(H13A,H13B), C35(H35A,H35B), C38(H38A,
 H38B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C6(H6), C18(H18), C5(H5), C27(H27), C25(H25), C40(H40), C19(H19),
 C20(H20), C24(H24), C21(H21), C41(H41), C3(H3), C42(H42), C2(H2), C43(H43)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C36(H36A,H36B,H36C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C)
;
_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
Br1 Br 0.46981(18) 0.54883(9) 0.37293(7) 0.1395(7) Uani 1 1 d . . . . .
O6 O 0.1743(5) 0.2615(4) 0.3021(2) 0.0584(14) Uani 1 1 d . . . . .
O2 O 0.6640(5) 0.3317(4) 0.2407(3) 0.0636(15) Uani 1 1 d . . . . .
O1 O 0.9202(6) 0.1456(4) 0.2656(3) 0.0709(16) Uani 1 1 d . . . . .
O5 O 0.4364(6) 0.2405(4) 0.1682(3) 0.0670(15) Uani 1 1 d . . . . .
N6 N 0.2731(6) 0.1722(4) 0.3285(3) 0.0511(16) Uani 1 1 d . . . . .
N5 N 0.3611(7) 0.0263(5) 0.4009(3) 0.0617(18) Uani 1 1 d . . . . .
N3 N 0.7682(6) 0.3424(5) 0.1742(3) 0.0580(17) Uani 1 1 d . . . . .
N2 N 0.8593(7) 0.3996(5) 0.0542(3) 0.0638(18) Uani 1 1 d . . . . .
C26 C 0.1244(8) 0.1283(5) 0.4601(3) 0.0522(19) Uani 1 1 d . . . . .
C29 C 0.2497(8) 0.1099(5) 0.3961(4) 0.0506(19) Uani 1 1 d . . . . .
C34 C 0.4820(8) 0.1614(6) 0.2106(4) 0.055(2) Uani 1 1 d . . . . .
N4 N -0.2138(9) 0.1623(6) 0.6521(4) 0.091(3) Uani 1 1 d . . . . .
C7 C 0.7435(8) 0.4168(6) 0.1117(4) 0.058(2) Uani 1 1 d . . . . .
C31 C 0.4544(8) 0.0361(5) 0.3333(4) 0.055(2) Uani 1 1 d . . . . .
C11 C 1.1446(8) 0.1452(6) 0.0744(4) 0.056(2) Uani 1 1 d . . . . .
C30 C 0.4053(8) 0.1276(5) 0.2862(3) 0.0504(19) Uani 1 1 d . . . . .
C9 C 0.9551(8) 0.3141(6) 0.0826(4) 0.059(2) Uani 1 1 d . . . . .
N1 N 0.2786(10) 0.7722(6) 0.0715(6) 0.107(3) Uani 1 1 d . . . . .
C28 C 0.1357(9) 0.0594(6) 0.5286(4) 0.066(2) Uani 1 1 d . . . . .
H28 H 0.219040 0.005929 0.531740 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6091(9) 0.5630(6) 0.0332(4) 0.060(2) Uani 1 1 d . . . . .
H6 H 0.679955 0.542544 -0.007849 0.072 Uiso 1 1 calc R U . . .
C8 C 0.9009(8) 0.2747(6) 0.1568(4) 0.054(2) Uani 1 1 d . . . . .
O7 O -0.3302(9) 0.2207(5) 0.6441(4) 0.124(3) Uani 1 1 d . . . . .
C39 C 0.1243(10) 0.4435(6) 0.2632(4) 0.067(2) Uani 1 1 d . . . . .
C4 C 0.6181(9) 0.5062(6) 0.1048(4) 0.062(2) Uani 1 1 d . . . . .
C12 C 0.9744(8) 0.1813(6) 0.2007(4) 0.0515(19) Uani 1 1 d . . . . .
C23 C -0.0941(9) 0.1503(6) 0.5848(4) 0.067(2) Uani 1 1 d . . . . .
O3 O 0.2854(9) 0.8268(6) 0.0107(5) 0.137(3) Uani 1 1 d . . . . .
C10 C 1.1023(9) 0.2651(6) 0.0403(4) 0.066(2) Uani 1 1 d . . . . .
H10A H 1.179325 0.301583 0.043769 0.079 Uiso 1 1 calc R U . . .
H10B H 1.096062 0.271880 -0.012725 0.079 Uiso 1 1 calc R U . . .
C32 C 0.5977(9) -0.0380(6) 0.3114(4) 0.073(3) Uani 1 1 d . . . . .
H32A H 0.586037 -0.109544 0.332900 0.087 Uiso 1 1 calc R U . . .
H32B H 0.676291 -0.022331 0.332041 0.087 Uiso 1 1 calc R U . . .
C17 C 0.6071(10) 0.3320(6) 0.3724(4) 0.069(2) Uani 1 1 d . . . . .
C13 C 1.1242(8) 0.1337(6) 0.1610(4) 0.059(2) Uani 1 1 d . . . . .
H13A H 1.144282 0.059352 0.181263 0.071 Uiso 1 1 calc R U . . .
H13B H 1.198825 0.165140 0.173149 0.071 Uiso 1 1 calc R U . . .
C33 C 0.6428(8) -0.0290(6) 0.2247(4) 0.062(2) Uani 1 1 d . . . . .
C35 C 0.6303(8) 0.0890(6) 0.1891(4) 0.067(2) Uani 1 1 d . . . . .
H35A H 0.707773 0.115615 0.203081 0.081 Uiso 1 1 calc R U . . .
H35B H 0.651041 0.093521 0.134470 0.081 Uiso 1 1 calc R U . . .
O8 O -0.1911(8) 0.1094(8) 0.7103(4) 0.144(4) Uani 1 1 d . . . . .
C18 C 0.6141(11) 0.2249(7) 0.4026(5) 0.080(3) Uani 1 1 d . . . . .
H18 H 0.685443 0.174637 0.379149 0.096 Uiso 1 1 calc R U . . .
C5 C 0.4969(10) 0.6495(6) 0.0214(5) 0.071(2) Uani 1 1 d . . . . .
H5 H 0.490590 0.686600 -0.026945 0.085 Uiso 1 1 calc R U . . .
C27 C 0.0262(9) 0.0697(7) 0.5909(4) 0.071(3) Uani 1 1 d . . . . .
H27 H 0.033168 0.023334 0.635948 0.085 Uiso 1 1 calc R U . . .
C25 C -0.0010(10) 0.2056(6) 0.4561(4) 0.079(3) Uani 1 1 d . . . . .
H25 H -0.011054 0.251022 0.410833 0.095 Uiso 1 1 calc R U . . .
C38 C 0.2265(10) 0.3568(6) 0.3020(4) 0.070(2) Uani 1 1 d . . . . .
H38A H 0.328354 0.353308 0.275088 0.084 Uiso 1 1 calc R U . . .
H38B H 0.222917 0.367272 0.353387 0.084 Uiso 1 1 calc R U . . .
C1 C 0.3969(9) 0.6788(6) 0.0820(5) 0.070(2) Uani 1 1 d . . . . .
C40 C 0.1347(11) 0.4522(6) 0.1862(4) 0.078(3) Uani 1 1 d . . . . .
H40 H 0.207000 0.405500 0.159791 0.093 Uiso 1 1 calc R U . . .
C19 C 0.5144(11) 0.1931(8) 0.4678(5) 0.084(3) Uani 1 1 d . . . . .
H19 H 0.522243 0.122033 0.487695 0.101 Uiso 1 1 calc R U . . .
C22 C 0.4973(10) 0.4042(7) 0.4091(5) 0.078(3) Uani 1 1 d . . . . .
C14 C 1.0483(10) 0.0819(7) 0.0515(5) 0.076(3) Uani 1 1 d . . . . .
H14A H 0.945102 0.107391 0.070329 0.114 Uiso 1 1 calc R U . . .
H14B H 1.075151 0.009114 0.072449 0.114 Uiso 1 1 calc R U . . .
H14C H 1.064014 0.089266 -0.002665 0.114 Uiso 1 1 calc R U . . .
C16 C 0.7145(10) 0.3592(7) 0.3027(4) 0.081(3) Uani 1 1 d . . . . .
H16A H 0.716522 0.433729 0.293904 0.097 Uiso 1 1 calc R U . . .
H16B H 0.814098 0.320123 0.307349 0.097 Uiso 1 1 calc R U . . .
C20 C 0.4081(13) 0.2638(10) 0.5016(5) 0.102(3) Uani 1 1 d . . . . .
H20 H 0.342739 0.241767 0.544695 0.122 Uiso 1 1 calc R U . . .
C24 C -0.1104(10) 0.2162(7) 0.5177(5) 0.084(3) Uani 1 1 d . . . . .
H24 H -0.195756 0.267772 0.514392 0.101 Uiso 1 1 calc R U . . .
C36 C 0.5433(11) -0.0786(7) 0.1924(5) 0.082(3) Uani 1 1 d . . . . .
H36A H 0.576899 -0.075700 0.138887 0.123 Uiso 1 1 calc R U . . .
H36B H 0.442373 -0.040951 0.201837 0.123 Uiso 1 1 calc R U . . .
H36C H 0.547769 -0.150592 0.216154 0.123 Uiso 1 1 calc R U . . .
C44 C 0.0129(12) 0.5169(7) 0.2998(4) 0.091(3) Uani 1 1 d . . . . .
C15 C 1.3094(9) 0.1074(7) 0.0422(5) 0.083(3) Uani 1 1 d . . . . .
H15A H 1.327000 0.129650 -0.011548 0.124 Uiso 1 1 calc R U . . .
H15B H 1.333562 0.032132 0.053137 0.124 Uiso 1 1 calc R U . . .
H15C H 1.370860 0.136946 0.065026 0.124 Uiso 1 1 calc R U . . .
C37 C 0.8065(9) -0.0845(7) 0.2053(5) 0.086(3) Uani 1 1 d . . . . .
H37A H 0.868548 -0.054830 0.227486 0.130 Uiso 1 1 calc R U . . .
H37B H 0.837486 -0.075160 0.151303 0.130 Uiso 1 1 calc R U . . .
H37C H 0.815355 -0.158190 0.224838 0.130 Uiso 1 1 calc R U . . .
C21 C 0.3956(12) 0.3700(10) 0.4723(5) 0.102(4) Uani 1 1 d . . . . .
H21 H 0.319350 0.418721 0.494656 0.123 Uiso 1 1 calc R U . . .
C41 C 0.0370(13) 0.5312(7) 0.1466(4) 0.093(3) Uani 1 1 d . . . . .
H41 H 0.043233 0.534616 0.094831 0.111 Uiso 1 1 calc R U . . .
O4 O 0.1774(11) 0.7895(7) 0.1226(6) 0.191(6) Uani 1 1 d . . . . .
C3 C 0.5123(12) 0.5371(8) 0.1644(5) 0.108(4) Uani 1 1 d . . . . .
H3 H 0.516279 0.498938 0.212611 0.129 Uiso 1 1 calc R U . . .
C42 C -0.0650(13) 0.6013(7) 0.1838(5) 0.106(4) Uani 1 1 d . . . . .
H42 H -0.126417 0.654667 0.157135 0.127 Uiso 1 1 calc R U . . .
C2 C 0.3999(11) 0.6235(8) 0.1545(5) 0.116(4) Uani 1 1 d . . . . .
H2 H 0.328285 0.644072 0.195173 0.139 Uiso 1 1 calc R U . . .
C43 C -0.0793(14) 0.5950(8) 0.2609(6) 0.125(5) Uani 1 1 d . . . . .
H43 H -0.150749 0.643205 0.286414 0.150 Uiso 1 1 calc R U . . .
Br2 Br -0.0074(2) 0.51237(13) 0.40535(6) 0.1754(9) Uani 1 1 d . . . . .


_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
Br1 C22 1.873(9) . ?
O6 N6 1.397(6) . ?
O6 C38 1.449(9) . ?
O2 N3 1.394(7) . ?
O2 C16 1.452(9) . ?
O1 C12 1.233(8) . ?
O5 C34 1.223(8) . ?
N6 C29 1.350(8) . ?
N6 C30 1.386(8) . ?
N5 C29 1.340(8) . ?
N5 C31 1.356(8) . ?
N3 C7 1.375(8) . ?
N3 C8 1.374(8) . ?
N2 C7 1.354(9) . ?
N2 C9 1.364(8) . ?
C26 C29 1.485(9) . ?
C26 C28 1.406(9) . ?
C26 C25 1.376(9) . ?
C34 C30 1.453(9) . ?
C34 C35 1.521(9) . ?
N4 O7 1.202(9) . ?
N4 C23 1.487(10) . ?
N4 O8 1.184(9) . ?
C7 C4 1.473(10) . ?
C31 C30 1.385(9) . ?
C31 C32 1.501(9) . ?
C11 C10 1.578(11) . ?
C11 C13 1.537(9) . ?
C11 C14 1.523(11) . ?
C11 C15 1.535(10) . ?
C9 C8 1.385(9) . ?
C9 C10 1.503(10) . ?
N1 O3 1.197(10) . ?
N1 C1 1.471(10) . ?
N1 O4 1.199(10) . ?
C28 H28 0.9300 . ?
C28 C27 1.367(10) . ?
C6 H6 0.9300 . ?
C6 C4 1.384(9) . ?
C6 C5 1.384(10) . ?
C8 C12 1.450(9) . ?
C39 C38 1.484(10) . ?
C39 C40 1.377(10) . ?
C39 C44 1.409(11) . ?
C4 C3 1.369(11) . ?
C12 C13 1.497(9) . ?
C23 C27 1.371(10) . ?
C23 C24 1.374(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.542(10) . ?
C17 C18 1.406(11) . ?
C17 C22 1.393(10) . ?
C17 C16 1.484(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C33 C35 1.556(10) . ?
C33 C36 1.517(12) . ?
C33 C37 1.540(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.405(12) . ?
C5 H5 0.9300 . ?
C5 C1 1.350(11) . ?
C27 H27 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.359(11) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C1 C2 1.385(11) . ?
C40 H40 0.9300 . ?
C40 C41 1.414(11) . ?
C19 H19 0.9300 . ?
C19 C20 1.341(12) . ?
C22 C21 1.402(14) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.388(14) . ?
C24 H24 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C44 C43 1.372(12) . ?
C44 Br2 1.891(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C21 H21 0.9300 . ?
C41 H41 0.9300 . ?
C41 C42 1.347(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.379(11) . ?
C42 H42 0.9300 . ?
C42 C43 1.378(12) . ?
C2 H2 0.9300 . ?
C43 H43 0.9300 . ?

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
N6 O6 C38 111.3(5) . . ?
N3 O2 C16 110.9(6) . . ?
C29 N6 O6 125.9(5) . . ?
C29 N6 C30 108.7(5) . . ?
C30 N6 O6 125.1(5) . . ?
C29 N5 C31 105.6(5) . . ?
C7 N3 O2 123.9(5) . . ?
C8 N3 O2 126.3(5) . . ?
C8 N3 C7 109.3(5) . . ?
C7 N2 C9 105.4(6) . . ?
C28 C26 C29 116.6(6) . . ?
C25 C26 C29 124.7(6) . . ?
C25 C26 C28 118.7(6) . . ?
N6 C29 C26 127.4(6) . . ?
N5 C29 N6 110.6(5) . . ?
N5 C29 C26 122.0(6) . . ?
O5 C34 C30 124.8(6) . . ?
O5 C34 C35 122.4(6) . . ?
C30 C34 C35 112.8(6) . . ?
O7 N4 C23 118.8(8) . . ?
O8 N4 O7 123.6(7) . . ?
O8 N4 C23 117.5(8) . . ?
N3 C7 C4 128.3(6) . . ?
N2 C7 N3 109.4(6) . . ?
N2 C7 C4 122.3(6) . . ?
N5 C31 C30 111.5(6) . . ?
N5 C31 C32 125.7(6) . . ?
C30 C31 C32 122.7(6) . . ?
C13 C11 C10 109.2(6) . . ?
C14 C11 C10 110.2(6) . . ?
C14 C11 C13 110.9(6) . . ?
C14 C11 C15 109.8(6) . . ?
C15 C11 C10 107.2(7) . . ?
C15 C11 C13 109.3(6) . . ?
N6 C30 C34 131.5(6) . . ?
C31 C30 N6 103.7(5) . . ?
C31 C30 C34 124.8(6) . . ?
N2 C9 C8 112.0(6) . . ?
N2 C9 C10 125.6(6) . . ?
C8 C9 C10 122.4(6) . . ?
O3 N1 C1 118.1(9) . . ?
O3 N1 O4 122.3(8) . . ?
O4 N1 C1 119.6(9) . . ?
C26 C28 H28 119.4 . . ?
C27 C28 C26 121.1(7) . . ?
C27 C28 H28 119.4 . . ?
C4 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C4 121.3(7) . . ?
N3 C8 C9 103.9(5) . . ?
N3 C8 C12 131.4(6) . . ?
C9 C8 C12 124.7(6) . . ?
C40 C39 C38 118.5(7) . . ?
C40 C39 C44 116.8(7) . . ?
C44 C39 C38 124.7(7) . . ?
C6 C4 C7 117.3(7) . . ?
C3 C4 C7 124.2(7) . . ?
C3 C4 C6 118.5(7) . . ?
O1 C12 C8 123.2(6) . . ?
O1 C12 C13 122.9(6) . . ?
C8 C12 C13 113.9(6) . . ?
C27 C23 N4 118.5(7) . . ?
C27 C23 C24 121.9(7) . . ?
C24 C23 N4 119.5(7) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 C11 110.2(6) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C31 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
C31 C32 C33 111.3(5) . . ?
H32A C32 H32B 108.0 . . ?
C33 C32 H32A 109.4 . . ?
C33 C32 H32B 109.4 . . ?
C18 C17 C16 117.5(7) . . ?
C22 C17 C18 117.4(8) . . ?
C22 C17 C16 125.0(8) . . ?
C11 C13 H13A 108.2 . . ?
C11 C13 H13B 108.2 . . ?
C12 C13 C11 116.4(6) . . ?
C12 C13 H13A 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C32 C33 C35 109.2(6) . . ?
C36 C33 C32 110.9(7) . . ?
C36 C33 C35 109.6(7) . . ?
C36 C33 C37 109.7(7) . . ?
C37 C33 C32 109.0(6) . . ?
C37 C33 C35 108.4(6) . . ?
C34 C35 C33 116.8(6) . . ?
C34 C35 H35A 108.1 . . ?
C34 C35 H35B 108.1 . . ?
C33 C35 H35A 108.1 . . ?
C33 C35 H35B 108.1 . . ?
H35A C35 H35B 107.3 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(8) . . ?
C19 C18 H18 119.6 . . ?
C6 C5 H5 120.8 . . ?
C1 C5 C6 118.3(7) . . ?
C1 C5 H5 120.8 . . ?
C28 C27 C23 118.0(7) . . ?
C28 C27 H27 121.0 . . ?
C23 C27 H27 121.0 . . ?
C26 C25 H25 119.7 . . ?
C24 C25 C26 120.5(7) . . ?
C24 C25 H25 119.7 . . ?
O6 C38 C39 105.7(7) . . ?
O6 C38 H38A 110.6 . . ?
O6 C38 H38B 110.6 . . ?
C39 C38 H38A 110.6 . . ?
C39 C38 H38B 110.6 . . ?
H38A C38 H38B 108.7 . . ?
C5 C1 N1 119.5(8) . . ?
C5 C1 C2 122.5(7) . . ?
C2 C1 N1 118.0(8) . . ?
C39 C40 H40 119.5 . . ?
C39 C40 C41 121.0(7) . . ?
C41 C40 H40 119.5 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(9) . . ?
C20 C19 H19 119.6 . . ?
C17 C22 Br1 122.1(7) . . ?
C17 C22 C21 120.6(9) . . ?
C21 C22 Br1 117.2(7) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C16 C17 106.8(8) . . ?
O2 C16 H16A 110.4 . . ?
O2 C16 H16B 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0(9) . . ?
C21 C20 H20 120.0 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.7(7) . . ?
C25 C24 H24 120.2 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C39 C44 Br2 119.7(6) . . ?
C43 C44 C39 122.1(8) . . ?
C43 C44 Br2 118.2(7) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.3(9) . . ?
C20 C21 H21 119.8 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.1(8) . . ?
C42 C41 H41 120.0 . . ?
C4 C3 H3 119.3 . . ?
C4 C3 C2 121.5(8) . . ?
C2 C3 H3 119.3 . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.7(8) . . ?
C43 C42 H42 119.7 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 117.9(8) . . ?
C3 C2 H2 121.0 . . ?
C44 C43 C42 119.4(9) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?

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
_geom_hbond_publ_flag
C25 H25 O6 0.93 2.35 2.990(9) 125.7 . yes
C3 H3 O2 0.93 2.35 2.990(10) 125.5 . yes

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
Br1 C22 C21 C20 179.2(8) . . . . ?
O6 N6 C29 N5 174.9(6) . . . . ?
O6 N6 C29 C26 -7.6(12) . . . . ?
O6 N6 C30 C34 5.5(13) . . . . ?
O6 N6 C30 C31 -173.7(6) . . . . ?
O2 N3 C7 N2 -173.7(7) . . . . ?
O2 N3 C7 C4 9.0(12) . . . . ?
O2 N3 C8 C9 174.2(7) . . . . ?
O2 N3 C8 C12 -4.6(13) . . . . ?
O1 C12 C13 C11 149.6(8) . . . . ?
O5 C34 C30 N6 -1.3(14) . . . . ?
O5 C34 C30 C31 177.8(8) . . . . ?
O5 C34 C35 C33 -151.1(8) . . . . ?
N6 O6 C38 C39 172.3(5) . . . . ?
N5 C31 C30 N6 -1.7(9) . . . . ?
N5 C31 C30 C34 179.0(7) . . . . ?
N5 C31 C32 C33 158.1(8) . . . . ?
N3 O2 C16 C17 -172.7(5) . . . . ?
N3 C7 C4 C6 -172.5(8) . . . . ?
N3 C7 C4 C3 8.6(15) . . . . ?
N3 C8 C12 O1 1.8(14) . . . . ?
N3 C8 C12 C13 -176.7(8) . . . . ?
N2 C7 C4 C6 10.5(12) . . . . ?
N2 C7 C4 C3 -168.4(10) . . . . ?
N2 C9 C8 N3 -2.0(9) . . . . ?
N2 C9 C8 C12 176.9(7) . . . . ?
N2 C9 C10 C11 -154.1(8) . . . . ?
C26 C28 C27 C23 -1.0(13) . . . . ?
C26 C25 C24 C23 1.2(15) . . . . ?
C29 N6 C30 C34 179.9(8) . . . . ?
C29 N6 C30 C31 0.6(8) . . . . ?
C29 N5 C31 C30 2.0(9) . . . . ?
C29 N5 C31 C32 179.1(8) . . . . ?
C29 C26 C28 C27 -179.9(8) . . . . ?
C29 C26 C25 C24 179.7(9) . . . . ?
N4 C23 C27 C28 -180.0(9) . . . . ?
N4 C23 C24 C25 179.9(9) . . . . ?
C7 N3 C8 C9 1.8(9) . . . . ?
C7 N3 C8 C12 -177.0(8) . . . . ?
C7 N2 C9 C8 1.4(10) . . . . ?
C7 N2 C9 C10 -179.2(8) . . . . ?
C7 C4 C3 C2 178.0(10) . . . . ?
C31 N5 C29 N6 -1.6(9) . . . . ?
C31 N5 C29 C26 -179.2(7) . . . . ?
C31 C32 C33 C35 47.7(9) . . . . ?
C31 C32 C33 C36 -73.2(9) . . . . ?
C31 C32 C33 C37 165.9(8) . . . . ?
C30 N6 C29 N5 0.6(9) . . . . ?
C30 N6 C29 C26 178.1(7) . . . . ?
C30 C34 C35 C33 30.6(10) . . . . ?
C30 C31 C32 C33 -25.2(11) . . . . ?
C9 N2 C7 N3 -0.3(9) . . . . ?
C9 N2 C7 C4 177.2(7) . . . . ?
C9 C8 C12 O1 -176.8(8) . . . . ?
C9 C8 C12 C13 4.7(11) . . . . ?
N1 C1 C2 C3 -178.9(11) . . . . ?
C28 C26 C29 N6 -171.2(8) . . . . ?
C28 C26 C29 N5 6.1(11) . . . . ?
C28 C26 C25 C24 1.2(14) . . . . ?
C6 C4 C3 C2 -0.9(17) . . . . ?
C6 C5 C1 N1 178.4(8) . . . . ?
C6 C5 C1 C2 -2.2(15) . . . . ?
C8 N3 C7 N2 -1.0(9) . . . . ?
C8 N3 C7 C4 -178.3(8) . . . . ?
C8 C9 C10 C11 25.2(11) . . . . ?
C8 C12 C13 C11 -32.0(10) . . . . ?
O7 N4 C23 C27 -167.6(9) . . . . ?
O7 N4 C23 C24 9.0(14) . . . . ?
C39 C40 C41 C42 2.1(16) . . . . ?
C39 C44 C43 C42 1.1(19) . . . . ?
C4 C6 C5 C1 1.1(13) . . . . ?
C4 C3 C2 C1 -0.1(18) . . . . ?
O3 N1 C1 C5 -8.9(15) . . . . ?
O3 N1 C1 C2 171.7(11) . . . . ?
C10 C11 C13 C12 54.3(9) . . . . ?
C10 C9 C8 N3 178.6(8) . . . . ?
C10 C9 C8 C12 -2.5(13) . . . . ?
C32 C31 C30 N6 -178.8(7) . . . . ?
C32 C31 C30 C34 1.9(13) . . . . ?
C32 C33 C35 C34 -53.3(10) . . . . ?
C17 C18 C19 C20 1.6(15) . . . . ?
C17 C22 C21 C20 3.5(15) . . . . ?
C13 C11 C10 C9 -48.2(9) . . . . ?
C35 C34 C30 N6 176.9(8) . . . . ?
C35 C34 C30 C31 -4.0(11) . . . . ?
O8 N4 C23 C27 8.8(14) . . . . ?
O8 N4 C23 C24 -174.5(10) . . . . ?
C18 C17 C22 Br1 -177.4(6) . . . . ?
C18 C17 C22 C21 -1.9(13) . . . . ?
C18 C17 C16 O2 73.8(9) . . . . ?
C18 C19 C20 C21 0.0(16) . . . . ?
C5 C6 C4 C7 -178.6(8) . . . . ?
C5 C6 C4 C3 0.4(13) . . . . ?
C5 C1 C2 C3 1.7(17) . . . . ?
C27 C23 C24 C25 -3.6(15) . . . . ?
C25 C26 C29 N6 10.2(13) . . . . ?
C25 C26 C29 N5 -172.5(8) . . . . ?
C25 C26 C28 C27 -1.3(13) . . . . ?
C38 O6 N6 C29 107.5(8) . . . . ?
C38 O6 N6 C30 -79.1(8) . . . . ?
C38 C39 C40 C41 178.0(9) . . . . ?
C38 C39 C44 C43 -179.5(11) . . . . ?
C38 C39 C44 Br2 2.9(14) . . . . ?
C40 C39 C38 O6 -72.0(9) . . . . ?
C40 C39 C44 C43 -1.4(16) . . . . ?
C40 C39 C44 Br2 -178.9(7) . . . . ?
C40 C41 C42 C43 -2.4(18) . . . . ?
C19 C20 C21 C22 -2.5(16) . . . . ?
C22 C17 C18 C19 -0.6(13) . . . . ?
C22 C17 C16 O2 -104.4(9) . . . . ?
C14 C11 C10 C9 73.8(8) . . . . ?
C14 C11 C13 C12 -67.3(9) . . . . ?
C16 O2 N3 C7 -112.6(8) . . . . ?
C16 O2 N3 C8 75.9(9) . . . . ?
C16 C17 C18 C19 -179.0(8) . . . . ?
C16 C17 C22 Br1 0.8(13) . . . . ?
C16 C17 C22 C21 176.3(9) . . . . ?
C24 C23 C27 C28 3.5(14) . . . . ?
C36 C33 C35 C34 68.4(8) . . . . ?
C44 C39 C38 O6 106.1(10) . . . . ?
C44 C39 C40 C41 -0.3(14) . . . . ?
C15 C11 C10 C9 -166.6(6) . . . . ?
C15 C11 C13 C12 171.4(8) . . . . ?
C37 C33 C35 C34 -171.9(7) . . . . ?
C41 C42 C43 C44 0.8(19) . . . . ?
O4 N1 C1 C5 169.1(12) . . . . ?
O4 N1 C1 C2 -10.3(17) . . . . ?
Br2 C44 C43 C42 178.8(10) . . . . ?

_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
;
