# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_UBJ-1072
_database_code_depnum_ccdc_archive 'CCDC 2401093'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2024-11-07 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        UBJ-1072
_chemical_formula_moiety         'C15 H11 F N2 O2'
_chemical_formula_sum            'C15 H11 F N2 O2'
_chemical_formula_weight         270.265
_chemical_oxdiff_formula         'C15 H11 F N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.1769(3)
_cell_length_b                   7.4272(2)
_cell_length_c                   18.6039(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.568(3)
_cell_angle_gamma                90
_cell_volume                     1242.25(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3296
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2340
_cell_measurement_theta_min      4.8260
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       prism
_exptl_crystal_F_000             562.135
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method -
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.9884
_diffrn_reflns_Laue_measured_fraction_max 0.9658
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5035
_diffrn_reflns_point_group_measured_fraction_full 0.9884
_diffrn_reflns_point_group_measured_fraction_max 0.9658
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.38
_diffrn_reflns_theta_min         4.85
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9658
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -18.00   1.00    1.25    --  -41.56 -57.00  30.00   96
  2  ω    -86.00 -51.00   1.00    1.25    --  -41.56 178.00-150.00   35
  3  ω    -18.00  32.00   1.00    1.25    --   41.56 -77.00-120.00   50
  4  ω     66.00 125.00   1.00    1.25    --   41.56 178.00 120.00   59
  5  ω    135.00 169.00   1.00    5.00    --  112.00  30.00 150.00   34
  6  ω     47.00 135.00   1.00    5.00    --  112.00 -45.00  30.00   88
  7  ω    143.00 174.00   1.00    5.00    --  112.00  15.00 120.00   31
  8  ω    112.00 172.00   1.00    5.00    --  112.00 125.00 -30.00   60
  9  ω     64.00  93.00   1.00    5.00    --  112.00 -61.00-120.00   29
 10  ω     92.00 118.00   1.00    5.00    --  112.00  30.00 150.00   26
 11  ω     56.00 126.00   1.00    5.00    --  112.00 -30.00-150.00   70
 12  ω    111.00 136.00   1.00    5.00    --  112.00  77.00   0.00   25
 13  ω     39.00  83.00   1.00    5.00    --  112.00-125.00 -60.00   44
 14  ω     64.00 140.00   1.00    5.00    --  112.00  15.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0024240000
_diffrn_orient_matrix_UB_12      0.0021027000
_diffrn_orient_matrix_UB_13      -0.0831035000
_diffrn_orient_matrix_UB_21      0.1146868000
_diffrn_orient_matrix_UB_22      -0.1540616000
_diffrn_orient_matrix_UB_23      0.0098221000
_diffrn_orient_matrix_UB_31      -0.1271319000
_diffrn_orient_matrix_UB_32      -0.1388283000
_diffrn_orient_matrix_UB_33      -0.0122788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          -
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -8
_reflns_number_gt                2208
_reflns_number_total             2514
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2852
_refine_diff_density_min         -0.3115
_refine_diff_density_rms         0.0669
_refine_ls_d_res_high            0.7932
_refine_ls_d_res_low             9.1130
_refine_ls_goodness_of_fit_ref   1.0548
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.0548
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.6355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1210
_refine_special_details          -
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.11955(12) 0.07844(14) 0.46960(6) 0.0293(3) Uani 1.000000 .
O1 O 0.44794(12) 0.25361(17) 0.12868(6) 0.0200(3) Uani 1.000000 .
N2 N 0.57793(13) 0.29075(17) 0.26915(7) 0.0144(3) Uani 1.000000 .
N1 N 0.36736(14) 0.19040(19) 0.18156(7) 0.0182(3) Uani 1.000000 .
C9 C 0.67105(16) 0.2975(2) 0.21981(8) 0.0164(3) Uani 1.000000 .
C7 C 0.43473(16) 0.21440(19) 0.24831(8) 0.0143(3) Uani 1.000000 .
C1 C 0.19443(18) 0.1049(2) 0.41489(9) 0.0203(3) Uani 1.000000 .
C4 C 0.35168(16) 0.1678(2) 0.30620(8) 0.0148(3) Uani 1.000000 .
C15 C 0.55979(16) 0.5066(2) 0.36655(9) 0.0167(3) Uani 1.000000 .
C6 C 0.33279(17) 0.0254(2) 0.42041(9) 0.0195(3) Uani 1.000000 .
C11 C 0.74315(16) 0.2683(2) 0.38907(9) 0.0157(3) Uani 1.000000 .
C8 C 0.60265(17) 0.2119(2) 0.14768(9) 0.0181(3) Uani 1.000000 .
C10 C 0.62835(15) 0.3576(2) 0.34296(8) 0.0138(3) Uani 1.000000 .
C5 C 0.41207(16) 0.0578(2) 0.36571(9) 0.0171(3) Uani 1.000000 .
C2 C 0.13000(17) 0.2094(2) 0.35592(10) 0.0220(4) Uani 1.000000 .
C3 C 0.20981(16) 0.2407(2) 0.30125(9) 0.0176(3) Uani 1.000000 .
O2 O 0.79429(13) 0.36542(18) 0.23349(7) 0.0240(3) Uani 1.000000 .
C13 C 0.72163(18) 0.4762(2) 0.48528(9) 0.0206(3) Uani 1.000000 .
C12 C 0.79072(17) 0.3291(2) 0.46035(9) 0.0193(3) Uani 1.000000 .
C14 C 0.60717(18) 0.5649(2) 0.43859(9) 0.0207(3) Uani 1.000000 .
H8a H 0.618(2) 0.078(3) 0.1523(12) 0.022(5) Uiso 1.000000 .
H11 H 0.788(2) 0.165(3) 0.3718(12) 0.026(5) Uiso 1.000000 .
H5 H 0.508(2) 0.004(3) 0.3653(11) 0.018(5) Uiso 1.000000 .
H14 H 0.558(2) 0.667(3) 0.4557(12) 0.024(5) Uiso 1.000000 .
H2 H 0.038(2) 0.261(3) 0.3542(12) 0.024(5) Uiso 1.000000 .
H3 H 0.169(2) 0.319(3) 0.2590(11) 0.015(4) Uiso 1.000000 .
H6 H 0.370(2) -0.051(3) 0.4603(12) 0.022(5) Uiso 1.000000 .
H15 H 0.476(2) 0.564(3) 0.3348(11) 0.018(5) Uiso 1.000000 .
H13 H 0.761(2) 0.525(3) 0.5365(13) 0.030(6) Uiso 1.000000 .
H12 H 0.868(2) 0.265(3) 0.4947(13) 0.027(6) Uiso 1.000000 .
H8b H 0.645(2) 0.261(3) 0.1088(13) 0.029(6) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3517(19) . ?
O1 N1 1.4237(18) . ?
O1 C8 1.4268(18) . ?
N2 C9 1.375(2) . ?
N2 C7 1.4123(18) . ?
N2 C10 1.4461(19) . ?
N1 C7 1.284(2) . ?
C9 C8 1.504(2) . ?
C9 O2 1.2176(19) . ?
C7 C4 1.480(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.377(2) . ?
C4 C5 1.398(2) . ?
C4 C3 1.396(2) . ?
C15 C10 1.387(2) . ?
C15 C14 1.393(2) . ?
C15 H15 0.97(2) . ?
C6 C5 1.386(2) . ?
C6 H6 0.94(2) . ?
C11 C10 1.387(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.96(2) . ?
C8 H8a 1.01(2) . ?
C8 H8b 0.96(2) . ?
C5 H5 0.97(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.92(2) . ?
C3 H3 0.99(2) . ?
C13 C12 1.389(2) . ?
C13 C14 1.388(2) . ?
C13 H13 1.02(2) . ?
C12 H12 0.98(2) . ?
C14 H14 0.97(2) . ?

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
C8 O1 N1 112.71(11) . . ?
C7 N2 C9 120.02(13) . . ?
C10 N2 C9 119.87(12) . . ?
C10 N2 C7 120.09(13) . . ?
C7 N1 O1 113.99(12) . . ?
C8 C9 N2 112.10(13) . . ?
O2 C9 N2 123.46(14) . . ?
O2 C9 C8 124.44(15) . . ?
N1 C7 N2 124.22(15) . . ?
C4 C7 N2 118.73(13) . . ?
C4 C7 N1 116.95(13) . . ?
C6 C1 F1 118.63(15) . . ?
C2 C1 F1 118.68(15) . . ?
C2 C1 C6 122.69(15) . . ?
C5 C4 C7 122.19(13) . . ?
C3 C4 C7 118.11(14) . . ?
C3 C4 C5 119.68(15) . . ?
C14 C15 C10 118.62(14) . . ?
H15 C15 C10 120.8(12) . . ?
H15 C15 C14 120.4(12) . . ?
C5 C6 C1 118.68(15) . . ?
H6 C6 C1 119.6(13) . . ?
H6 C6 C5 121.7(13) . . ?
C12 C11 C10 119.38(15) . . ?
H11 C11 C10 120.0(13) . . ?
H11 C11 C12 120.6(13) . . ?
C9 C8 O1 110.22(13) . . ?
H8a C8 O1 110.8(12) . . ?
H8a C8 C9 108.4(12) . . ?
H8b C8 O1 105.1(13) . . ?
H8b C8 C9 110.6(14) . . ?
H8b C8 H8a 111.7(18) . . ?
C15 C10 N2 119.68(13) . . ?
C11 C10 N2 118.82(14) . . ?
C11 C10 C15 121.49(14) . . ?
C6 C5 C4 120.01(14) . . ?
H5 C5 C4 116.8(12) . . ?
H5 C5 C6 123.1(12) . . ?
C3 C2 C1 118.23(15) . . ?
H2 C2 C1 120.4(14) . . ?
H2 C2 C3 121.3(14) . . ?
C2 C3 C4 120.64(15) . . ?
H3 C3 C4 118.6(11) . . ?
H3 C3 C2 120.8(11) . . ?
C14 C13 C12 120.24(15) . . ?
H13 C13 C12 119.6(13) . . ?
H13 C13 C14 119.9(13) . . ?
C13 C12 C11 119.90(14) . . ?
H12 C12 C11 121.0(13) . . ?
H12 C12 C13 118.9(13) . . ?
C13 C14 C15 120.36(15) . . ?
H14 C14 C15 119.0(13) . . ?
H14 C14 C13 120.6(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C6 C5 -177.64(14) . . . . ?
F1 C1 C2 C3 177.90(14) . . . . ?
O1 N1 C7 N2 -2.00(15) . . . . ?
O1 N1 C7 C4 174.36(12) . . . . ?
O1 C8 C9 N2 38.80(14) . . . . ?
O1 C8 C9 O2 -141.16(13) . . . . ?
N2 C7 C4 C5 -53.82(16) . . . . ?
N2 C7 C4 C3 124.70(14) . . . . ?
N2 C10 C15 C14 178.00(14) . . . . ?
N2 C10 C11 C12 -178.87(14) . . . . ?
N1 C7 C4 C5 129.61(14) . . . . ?
N1 C7 C4 C3 -51.87(16) . . . . ?
C7 C4 C5 C6 176.79(14) . . . . ?
C7 C4 C3 C2 -176.58(14) . . . . ?
C1 C6 C5 C4 -0.44(18) . . . . ?
C1 C2 C3 C4 -0.06(19) . . . . ?
C15 C10 C11 C12 -0.03(17) . . . . ?
C15 C14 C13 C12 0.49(19) . . . . ?
C11 C12 C13 C14 -1.36(18) . . . . ?


_olex2_exptl_crystal_mounting_method -
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.616
_oxdiff_exptl_absorpt_empirical_full_min 0.598
_chemical_name_common            
3-(4-fluorophenyl)-4-phenyl-4H-1,2,4-oxadiazin-5(6H)-one
####################################################################### 
# 
# 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_UBJ-760
_database_code_depnum_ccdc_archive 'CCDC 2404214'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        
3-(4-fluorophenyl)-4H-1,2,4-oxadiazin-5(6H)-one
_chemical_formula_moiety         'C9 H7 F N2 O2'
_chemical_formula_sum            'C9 H7 F N2 O2'
_chemical_formula_weight         194.167
_chemical_oxdiff_formula         'C9 H7 F N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

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

_symmetry_Int_Tables_number      2
_cell_length_a                   6.9399(3)
_cell_length_b                   7.2091(4)
_cell_length_c                   9.0838(4)
_cell_angle_alpha                88.303(4)
_cell_angle_beta                 68.988(4)
_cell_angle_gamma                76.975(4)
_cell_volume                     412.67(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    99.98(19)
_cell_measurement_theta_max      68.9570
_cell_measurement_theta_min      5.2160
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       prism
_exptl_crystal_F_000             200.837
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.9779
_diffrn_reflns_Laue_measured_fraction_max 0.9746
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2997
_diffrn_reflns_point_group_measured_fraction_full 0.9779
_diffrn_reflns_point_group_measured_fraction_max 0.9746
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.12
_diffrn_reflns_theta_min         5.22
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(19)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9779
_diffrn_measured_fraction_theta_max 0.9746
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -56.00   0.50    0.25    --  -35.49 -60.00 -24.00   92
  2  ω      0.00  26.00   0.50    0.25    --  -35.49  60.00 114.00   52
  3  ω    -26.00  40.00   0.50    0.25    --   35.49 -60.00 -24.00  132
  4  ω     57.00  82.00   0.50    0.25    --   35.49  60.00 114.00   50
  5  ω     33.00 113.00   0.50    1.00    --  100.00 -60.00 -24.00  160
  6  ω     94.00 157.00   0.50    1.00    --  100.00  60.00 114.00  126
  7  ω   -103.00 -35.00   0.50    0.25    --  -35.49 -65.00-120.00  136
  8  ω   -101.00 -59.00   0.50    0.25    --  -35.49 -65.00 120.00   84
  9  ω    -35.00 -10.00   0.50    0.25    --  -35.49 -21.00 -60.00   50
 10  ω    -68.00 -43.00   0.50    0.25    --  -35.49 -21.00 -60.00   50
 11  ω    -54.00  -9.00   0.50    0.25    --  -35.49 -65.00 120.00   90
 12  ω     46.00  95.00   0.50    0.25    --   35.49-138.00   0.00   98
 13  ω    -31.00  51.00   0.50    0.25    --   35.49 -65.00-180.00  164
 14  ω    -24.00   4.00   0.50    0.25    --   35.49 -89.00  90.00   56
 15  ω    -12.00  53.00   0.50    0.25    --   35.49-104.00  60.00  130
 16  ω     11.00  52.00   0.50    0.25    --   35.49 -89.00  90.00   82
 17  ω     49.00  74.00   0.50    0.25    --   35.49  43.00-150.00   50
 18  ω     51.00  78.00   0.50    0.25    --   35.49-138.00-120.00   54
 19  ω    -32.00  58.00   0.50    0.25    --   35.49 -54.00 -90.00  180
 20  ω     68.00  99.00   0.50    1.00    --  100.00-149.00-120.00   62
 21  ω    129.00 155.00   0.50    1.00    --  100.00  77.00  60.00   52
 22  ω     33.00  63.00   0.50    1.00    --  100.00-149.00-120.00   60
 23  ω     92.00 123.00   0.50    1.00    --  100.00 -53.00-180.00   62
 24  ω     83.00 125.00   0.50    1.00    --  100.00  77.00  60.00   84
 25  ω     83.00 156.00   0.50    1.00    --  100.00  77.00  30.00  146
 26  ω     60.00  87.00   0.50    1.00    --  100.00 -91.00   0.00   54
 27  ω     25.00  54.00   0.50    1.00    --  100.00 -91.00   0.00   58
 28  ω     33.00  88.00   0.50    1.00    --  100.00 -53.00-180.00  110
 29  ω     74.00 124.00   0.50    1.00    --  100.00  69.00   0.00  100
 30  ω     66.00 118.00   0.50    1.00    --  100.00 -37.00  60.00  104
 31  ω     34.00  67.00   0.50    1.00    --  100.00-107.00 -60.00   66
 32  ω     74.00 103.00   0.50    1.00    --  100.00-107.00 -60.00   58
 33  ω    108.00 142.00   0.50    1.00    --  100.00  91.00   0.00   68
 34  ω     43.00 103.00   0.50    1.00    --  100.00-107.00 120.00  120
 35  ω     28.00 128.00   0.50    1.00    --  100.00 -22.00   0.00  200
 36  ω     61.00 103.00   0.50    1.00    --  100.00 -91.00 -30.00   84
 37  ω    123.00 149.00   0.50    1.00    --  100.00 149.00 -90.00   52
 38  ω     91.00 125.00   0.50    1.00    --  100.00 -61.00-150.00   68
 39  ω    129.00 154.00   0.50    1.00    --  100.00  15.00 -30.00   50
 40  ω     65.00 113.00   0.50    1.00    --  100.00  15.00 -30.00   96
 41  ω     60.00 108.00   0.50    1.00    --  100.00 -30.00 -60.00   96
 42  ω     22.00  54.00   0.50    1.00    --  100.00 -91.00 -30.00   64
 43  ω    113.00 153.00   0.50    1.00    --  100.00 125.00-120.00   80
 44  ω     70.00 112.00   0.50    1.00    --  100.00-125.00-120.00   84
 45  ω     33.00  60.00   0.50    1.00    --  100.00-125.00-120.00   54
 46  ω     81.00 107.00   0.50    1.00    --  100.00 125.00-120.00   52
 47  ω     94.00 128.00   0.50    1.00    --  100.00-149.00 150.00   68
 48  ω     89.00 126.00   0.50    1.00    --  100.00  91.00-150.00   74
 49  ω     81.00 150.00   0.50    1.00    --  100.00  53.00   0.00  138
 50  ω     67.00 110.00   0.50    1.00    --  100.00 -77.00-150.00   86
 51  ω     37.00  62.00   0.50    1.00    --  100.00-125.00-180.00   50
 52  ω     71.00  96.00   0.50    1.00    --  100.00-125.00-180.00   50
 53  ω     67.00  99.00   0.50    1.00    --  100.00 149.00 -90.00   64
 54  ω     96.00 122.00   0.50    1.00    --  100.00 107.00-120.00   52
 55  ω     65.00  94.00   0.50    1.00    --  100.00 -91.00-150.00   58
 56  ω     34.00  61.00   0.50    1.00    --  100.00 -91.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0044968000
_diffrn_orient_matrix_UB_12      0.1825171000
_diffrn_orient_matrix_UB_13      -0.0925149000
_diffrn_orient_matrix_UB_21      -0.1194239000
_diffrn_orient_matrix_UB_22      -0.0753192000
_diffrn_orient_matrix_UB_23      -0.0903977000
_diffrn_orient_matrix_UB_31      -0.2131437000
_diffrn_orient_matrix_UB_32      0.0963215000
_diffrn_orient_matrix_UB_33      0.1279834000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          -
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1317
_reflns_number_total             1499
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.2165
_refine_diff_density_min         -0.2854
_refine_diff_density_rms         0.0632
_refine_ls_d_res_high            0.8251
_refine_ls_d_res_low             8.4664
_refine_ls_goodness_of_fit_ref   1.0873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    11
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.0873
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.0391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          -
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2a), C5(H5), C6(H6)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.27407(14) 0.45578(13) 0.32475(10) 0.0327(3) Uani 1.000000 .
O1 O 0.06271(14) -0.30244(14) 0.93470(11) 0.0230(3) Uani 1.000000 .
O2 O 0.43253(15) -0.20293(13) 1.08815(11) 0.0244(3) Uani 1.000000 .
N2 N 0.30616(17) -0.05570(16) 0.90586(13) 0.0195(3) Uani 1.000000 .
N1 N 0.09164(17) -0.18383(16) 0.80335(13) 0.0211(3) Uani 1.000000 .
C3 C 0.22407(19) 0.0200(2) 0.52686(16) 0.0215(3) Uani 1.000000 .
H3 H 0.21047(19) -0.1046(2) 0.50848(16) 0.0258(4) Uiso 1.000000 R
C7 C 0.20798(19) -0.06588(18) 0.79764(15) 0.0182(3) Uani 1.000000 .
C4 C 0.23139(19) 0.07160(19) 0.67159(15) 0.0188(3) Uani 1.000000 .
C8 C 0.2464(2) -0.36530(19) 0.97618(16) 0.0224(3) Uani 1.000000 .
H8a H 0.2085(2) -0.43384(19) 1.07486(16) 0.0268(4) Uiso 1.000000 R
H8b H 0.3562(2) -0.45557(19) 0.89167(16) 0.0268(4) Uiso 1.000000 R
C1 C 0.2586(2) 0.3284(2) 0.43965(16) 0.0242(3) Uani 1.000000 .
C9 C 0.3350(2) -0.20153(18) 0.99914(15) 0.0196(3) Uani 1.000000 .
C2 C 0.2366(2) 0.1497(2) 0.41021(16) 0.0237(3) Uani 1.000000 .
H2a H 0.2301(2) 0.1161(2) 0.31204(16) 0.0285(4) Uiso 1.000000 R
C5 C 0.2524(2) 0.2547(2) 0.69735(16) 0.0221(3) Uani 1.000000 .
H5 H 0.2574(2) 0.2901(2) 0.79557(16) 0.0265(4) Uiso 1.000000 R
C6 C 0.2659(2) 0.3856(2) 0.58086(17) 0.0253(3) Uani 1.000000 .
H6 H 0.2798(2) 0.5106(2) 0.59782(17) 0.0304(4) Uiso 1.000000 R
H2 H 0.379(3) 0.035(3) 0.901(2) 0.028(4) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3605(16) . ?
O1 N1 1.4284(14) . ?
O1 C8 1.4306(15) . ?
O2 C9 1.2253(17) . ?
N2 C7 1.3939(17) . ?
N2 C9 1.3555(17) . ?
N2 H2 0.90(2) . ?
N1 C7 1.2863(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3981(19) . ?
C3 C2 1.3846(19) . ?
C7 C4 1.4805(17) . ?
C4 C5 1.395(2) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.4996(19) . ?
C1 C2 1.376(2) . ?
C1 C6 1.380(2) . ?
C2 H2a 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3889(19) . ?
C6 H6 0.9500 . ?

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
C8 O1 N1 114.54(9) . . ?
C9 N2 C7 121.34(11) . . ?
H2 N2 C7 120.6(12) . . ?
H2 N2 C9 116.6(12) . . ?
C7 N1 O1 114.59(11) . . ?
C4 C3 H3 119.85(8) . . ?
C2 C3 H3 119.85(8) . . ?
C2 C3 C4 120.29(13) . . ?
N1 C7 N2 123.98(12) . . ?
C4 C7 N2 118.46(11) . . ?
C4 C7 N1 117.52(11) . . ?
C7 C4 C3 119.58(12) . . ?
C5 C4 C3 119.49(12) . . ?
C5 C4 C7 120.89(12) . . ?
H8a C8 O1 109.29(6) . . ?
H8b C8 O1 109.29(7) . . ?
H8b C8 H8a 107.9 . . ?
C9 C8 O1 111.67(11) . . ?
C9 C8 H8a 109.29(7) . . ?
C9 C8 H8b 109.29(7) . . ?
C2 C1 F1 118.86(12) . . ?
C6 C1 F1 118.00(13) . . ?
C6 C1 C2 123.14(13) . . ?
N2 C9 O2 123.16(12) . . ?
C8 C9 O2 123.30(12) . . ?
C8 C9 N2 113.46(11) . . ?
C1 C2 C3 118.51(13) . . ?
H2a C2 C3 120.74(8) . . ?
H2a C2 C1 120.74(8) . . ?
H5 C5 C4 119.67(8) . . ?
C6 C5 C4 120.67(13) . . ?
C6 C5 H5 119.67(8) . . ?
C5 C6 C1 117.89(14) . . ?
H6 C6 C1 121.05(9) . . ?
H6 C6 C5 121.05(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 179.05(11) . . . . ?
F1 C1 C6 C5 -179.32(12) . . . . ?
O1 N1 C7 N2 2.17(13) . . . . ?
O1 N1 C7 C4 -175.44(9) . . . . ?
O1 C8 C9 O2 151.37(10) . . . . ?
O1 C8 C9 N2 -31.83(12) . . . . ?
O2 C9 N2 C7 175.13(12) . . . . ?
N2 C7 C4 C3 151.26(11) . . . . ?
N2 C7 C4 C5 -31.26(13) . . . . ?
N1 C7 C4 C3 -30.99(14) . . . . ?
N1 C7 C4 C5 146.48(12) . . . . ?
C3 C4 C5 C6 0.02(14) . . . . ?
C3 C2 C1 C6 -0.91(15) . . . . ?
C7 C4 C5 C6 -177.46(12) . . . . ?
C4 C5 C6 C1 -0.18(14) . . . . ?


_olex2_exptl_crystal_mounting_method -
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.583
_oxdiff_exptl_absorpt_empirical_full_min 0.690
####################################################################### 
# 
# 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_UBJ-1124
_database_code_depnum_ccdc_archive 'CCDC 2401094'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2024-11-07 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        UBJ-1124
_chemical_formula_moiety         'C15 H11 Br N2 O2'
_chemical_formula_sum            'C15 H11 Br N2 O2'
_chemical_formula_weight         331.170
_chemical_oxdiff_formula         'C15 H11 Br N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.66955 1.28295 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

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

_symmetry_Int_Tables_number      2
_cell_length_a                   5.7761(3)
_cell_length_b                   9.1850(4)
_cell_length_c                   12.8929(4)
_cell_angle_alpha                105.632(3)
_cell_angle_beta                 92.203(3)
_cell_angle_gamma                100.013(4)
_cell_volume                     646.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5469
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4650
_cell_measurement_theta_min      3.6340
_exptl_absorpt_coefficient_mu    4.368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       prism
_exptl_crystal_F_000             331.620
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.9772
_diffrn_reflns_Laue_measured_fraction_max 0.9742
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6851
_diffrn_reflns_point_group_measured_fraction_full 0.9772
_diffrn_reflns_point_group_measured_fraction_max 0.9742
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9772
_diffrn_measured_fraction_theta_max 0.9742
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -43.00   0.50    0.20    -- -106.00  61.00-148.00   56
  2  ω    -39.00  24.00   0.50    0.05    --  -47.14  61.00-148.00  126
  3  ω    -68.00 -41.00   0.50    0.20    -- -106.00  61.00 -30.00   54
  4  ω    -67.00 -42.00   0.50    0.20    -- -106.00  61.00   0.00   50
  5  ω    -71.00 -35.00   0.50    0.20    -- -106.00  61.00  60.00   72
  6  ω    -16.00  14.00   0.50    0.05    --  -47.14  19.00   0.00   60
  7  ω    -17.00  24.00   0.50    0.05    --   47.14 -19.00  60.00   82
  8  ω     -9.00  19.00   0.50    0.05    --   47.14 -19.00 120.00   56
  9  ω    -13.00  14.00   0.50    0.05    --   47.14 -61.00  72.00   54
 10  ω     20.00  64.00   0.50    0.05    --   47.14 -61.00  72.00   88
 11  ω     68.00 110.00   0.50    0.20    --  113.25-125.00 150.00   84
 12  ω     77.00 104.00   0.50    0.20    --  113.25 -94.00 120.00   54
 13  ω     84.00 109.00   0.50    0.20    --  113.25-125.00  60.00   50
 14  ω     52.00  95.00   0.50    0.20    --  113.25 -94.00  60.00   86
 15  ω     62.00 103.00   0.50    0.20    --  113.25 -94.00 -30.00   82
 16  ω     45.00  86.00   0.50    0.20    --  113.25-125.00-120.00   82
 17  ω     74.00 110.00   0.50    0.20    --  113.25-125.00-150.00   72
 18  ω     50.00 102.00   0.50    0.20    --  113.25 -94.00-120.00  104
 19  ω     81.00 106.00   0.50    0.20    --  113.25 -77.00-120.00   50
 20  ω     42.00  67.00   0.50    0.20    --  113.25 -61.00-120.00   50
 21  ω     43.00  68.00   0.50    0.20    --  113.25 -61.00   0.00   50
 22  ω     42.00  67.00   0.50    0.20    --  113.25 -61.00  60.00   50
 23  ω     42.00  67.00   0.50    0.20    --  113.25 -61.00  72.00   50
 24  ω     44.00  69.00   0.50    0.20    --  113.25 -61.00  90.00   50
 25  ω     43.00  69.00   0.50    0.20    --  113.25 -61.00 120.00   52
 26  ω    140.00 178.00   0.50    0.20    --  113.25  15.00   0.00   76
 27  ω    122.00 169.00   0.50    0.20    --  113.25  45.00 150.00   94
 28  ω    100.00 178.00   0.50    0.20    --  113.25  15.00 120.00  156
 29  ω    102.00 169.00   0.50    0.20    --  113.25  61.00-148.00  134
 30  ω     70.00 117.00   0.50    0.05    --   47.14  61.00-148.00   94
 31  ω     33.00  67.00   0.50    0.05    --   47.14  61.00-148.00   68
 32  ω    -89.00 -16.00   0.50    0.05    --  -47.14 125.00 -30.00  146
 33  ω    -73.00 -37.00   0.50    0.20    -- -106.00 113.00-135.10   72
 34  ω    -71.00 -38.00   0.50    0.20    -- -106.00 125.00 -30.00   66
 35  ω   -112.00 -73.00   0.50    0.20    -- -106.00 125.00 -30.00   78
 36  ω   -108.00 -82.00   0.50    0.20    -- -106.00 113.00-135.10   52
 37  ω   -107.00 -78.00   0.50    0.20    -- -106.00 108.00 -39.80   58
 38  ω    -63.00 -36.00   0.50    0.20    -- -106.00 108.00 -39.80   54
 39  ω   -112.00 -86.00   0.50    0.20    -- -106.00 125.00  60.00   52
 40  ω    -62.00 -36.00   0.50    0.20    -- -106.00 125.00 150.00   52
 41  ω   -150.00 -96.00   0.50    0.20    -- -106.00 -30.00 -90.00  108
 42  ω   -133.00-107.00   0.50    0.20    -- -106.00 -61.00-180.00   52
 43  ω   -175.00-136.00   0.50    0.20    -- -106.00 -61.00-180.00   78
 44  ω   -106.00 -37.00   0.50    0.05    --  -47.14 -61.00  72.00  138
 45  ω   -147.00 -89.00   0.50    0.20    -- -106.00 -61.00  72.00  116
 46  ω   -176.00 -89.00   0.50    0.20    -- -106.00 -61.00 150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2082638000
_diffrn_orient_matrix_UB_12      -0.1182241000
_diffrn_orient_matrix_UB_13      -0.0698923000
_diffrn_orient_matrix_UB_21      -0.1733868000
_diffrn_orient_matrix_UB_22      0.1000480000
_diffrn_orient_matrix_UB_23      0.0549640000
_diffrn_orient_matrix_UB_31      0.0226755000
_diffrn_orient_matrix_UB_32      0.0866146000
_diffrn_orient_matrix_UB_33      -0.0872643000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          -
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2311
_reflns_number_total             2382
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.0018
_refine_diff_density_min         -0.4183
_refine_diff_density_rms         0.1087
_refine_ls_d_res_high            0.8204
_refine_ls_d_res_low             12.3657
_refine_ls_goodness_of_fit_ref   1.0424
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.0424
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          -
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C14(H14), C15(H15), C5(H5), C11(H11), C13(H13),
 C12(H12)
;
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_refinement_flags_posn
Br1 Br 1.14954(3) 0.25447(2) 0.025271(14) 0.02145(12) Uani 1.000000 .
O2 O 0.2712(2) 0.88975(16) 0.44998(11) 0.0187(3) Uani 1.000000 .
O1 O 0.6799(3) 0.74103(17) 0.57841(11) 0.0212(3) Uani 1.000000 .
N1 N 0.7677(3) 0.6443(2) 0.48947(14) 0.0194(3) Uani 1.000000 .
N2 N 0.5712(3) 0.76863(19) 0.38257(13) 0.0158(3) Uani 1.000000 .
C4 C 0.8168(3) 0.5709(2) 0.30368(16) 0.0169(4) Uani 1.000000 .
C7 C 0.7173(3) 0.6664(2) 0.39731(15) 0.0161(4) Uani 1.000000 .
C2 C 1.1118(3) 0.4160(2) 0.24355(16) 0.0184(4) Uani 1.000000 .
H2 H 1.2447(3) 0.3749(2) 0.25908(16) 0.0221(5) Uiso 1.000000 R
C6 C 0.8185(4) 0.4416(2) 0.11338(16) 0.0201(4) Uani 1.000000 .
H6 H 0.7530(4) 0.4179(2) 0.04071(16) 0.0241(5) Uiso 1.000000 R
C3 C 1.0124(4) 0.5085(2) 0.32570(16) 0.0185(4) Uani 1.000000 .
H3 H 1.0773(4) 0.5303(2) 0.39830(16) 0.0223(5) Uiso 1.000000 R
C9 C 0.4128(3) 0.8109(2) 0.45927(15) 0.0161(4) Uani 1.000000 .
C14 C 0.8553(4) 1.0228(2) 0.22451(16) 0.0192(4) Uani 1.000000 .
H14 H 1.0061(4) 1.0813(2) 0.22113(16) 0.0231(5) Uiso 1.000000 R
C15 C 0.8255(3) 0.9371(2) 0.29883(15) 0.0172(4) Uani 1.000000 .
H15 H 0.9544(3) 0.9383(2) 0.34729(15) 0.0207(4) Uiso 1.000000 R
C5 C 0.7198(4) 0.5345(2) 0.19716(16) 0.0186(4) Uani 1.000000 .
H5 H 0.5846(4) 0.5734(2) 0.18145(16) 0.0223(5) Uiso 1.000000 R
C1 C 1.0146(4) 0.3842(2) 0.13796(16) 0.0179(4) Uani 1.000000 .
C8 C 0.4391(4) 0.7475(2) 0.55479(15) 0.0185(4) Uani 1.000000 .
H8a H 0.3413(4) 0.6429(2) 0.53860(15) 0.0222(5) Uiso 1.000000 R
H8b H 0.3820(4) 0.8139(2) 0.61875(15) 0.0222(5) Uiso 1.000000 R
C11 C 0.4132(4) 0.8460(2) 0.23041(16) 0.0185(4) Uani 1.000000 .
H11 H 0.2640(4) 0.7840(2) 0.23181(16) 0.0222(5) Uiso 1.000000 R
C10 C 0.6042(3) 0.8498(2) 0.30106(15) 0.0161(4) Uani 1.000000 .
C13 C 0.6645(4) 1.0231(2) 0.15509(16) 0.0199(4) Uani 1.000000 .
H13 H 0.6845(4) 1.0839(2) 0.10586(16) 0.0238(5) Uiso 1.000000 R
C12 C 0.4439(4) 0.9341(2) 0.15781(16) 0.0198(4) Uani 1.000000 .
H12 H 0.3145(4) 0.9337(2) 0.10993(16) 0.0238(5) Uiso 1.000000 R


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 C1 1.901(2) . ?
O2 C9 1.205(3) . ?
O1 N1 1.419(2) . ?
O1 C8 1.427(3) . ?
N1 C7 1.289(3) . ?
N2 C7 1.410(2) . ?
N2 C9 1.397(3) . ?
N2 C10 1.444(2) . ?
C4 C7 1.488(3) . ?
C4 C3 1.405(3) . ?
C4 C5 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C2 C1 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.393(3) . ?
C6 C1 1.390(3) . ?
C3 H3 0.9500 . ?
C9 C8 1.510(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C14 C13 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C10 1.392(3) . ?
C5 H5 0.9500 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C11 H11 0.9500 . ?
C11 C10 1.393(3) . ?
C11 C12 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.396(3) . ?
C12 H12 0.9500 . ?

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
C8 O1 N1 111.40(14) . . ?
C7 N1 O1 114.57(16) . . ?
C9 N2 C7 118.84(15) . . ?
C10 N2 C7 122.33(16) . . ?
C10 N2 C9 118.11(15) . . ?
C3 C4 C7 117.50(18) . . ?
C5 C4 C7 123.65(18) . . ?
C5 C4 C3 118.77(19) . . ?
N2 C7 N1 123.73(18) . . ?
C4 C7 N1 115.39(17) . . ?
C4 C7 N2 120.84(16) . . ?
C3 C2 H2 120.52(11) . . ?
C1 C2 H2 120.52(12) . . ?
C1 C2 C3 118.96(18) . . ?
C5 C6 H6 120.59(11) . . ?
C1 C6 H6 120.59(12) . . ?
C1 C6 C5 118.83(18) . . ?
C2 C3 C4 121.05(18) . . ?
H3 C3 C4 119.48(12) . . ?
H3 C3 C2 119.48(11) . . ?
N2 C9 O2 123.45(16) . . ?
C8 C9 O2 123.87(18) . . ?
C8 C9 N2 112.67(16) . . ?
C15 C14 H14 119.89(12) . . ?
C13 C14 H14 119.89(11) . . ?
C13 C14 C15 120.21(18) . . ?
H15 C15 C14 120.49(12) . . ?
C10 C15 C14 119.02(18) . . ?
C10 C15 H15 120.49(11) . . ?
C6 C5 C4 120.80(19) . . ?
H5 C5 C4 119.60(12) . . ?
H5 C5 C6 119.60(11) . . ?
C2 C1 Br1 118.80(16) . . ?
C6 C1 Br1 119.61(15) . . ?
C6 C1 C2 121.57(19) . . ?
C9 C8 O1 110.74(16) . . ?
H8a C8 O1 109.50(10) . . ?
H8a C8 C9 109.50(11) . . ?
H8b C8 O1 109.50(10) . . ?
H8b C8 C9 109.50(11) . . ?
H8b C8 H8a 108.1 . . ?
C10 C11 H11 120.47(11) . . ?
C12 C11 H11 120.47(12) . . ?
C12 C11 C10 119.06(18) . . ?
C15 C10 N2 118.67(17) . . ?
C11 C10 N2 119.82(17) . . ?
C11 C10 C15 121.43(17) . . ?
H13 C13 C14 119.97(11) . . ?
C12 C13 C14 120.06(17) . . ?
C12 C13 H13 119.97(11) . . ?
C13 C12 C11 120.18(18) . . ?
H12 C12 C11 119.91(12) . . ?
H12 C12 C13 119.91(11) . . ?

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 C1 C2 C3 -179.16(14) . . . . ?
Br1 C1 C6 C5 179.00(15) . . . . ?
O2 C9 N2 C7 -175.20(19) . . . . ?
O2 C9 N2 C10 14.3(2) . . . . ?
O2 C9 C8 O1 -146.0(2) . . . . ?
O1 N1 C7 N2 -4.92(19) . . . . ?
O1 N1 C7 C4 177.40(15) . . . . ?
O1 C8 C9 N2 33.88(18) . . . . ?
N1 C7 N2 C9 -21.5(2) . . . . ?
N1 C7 N2 C10 148.54(19) . . . . ?
N1 C7 C4 C3 -21.0(2) . . . . ?
N1 C7 C4 C5 155.67(18) . . . . ?
N2 C7 C4 C3 161.20(18) . . . . ?
N2 C7 C4 C5 -22.1(2) . . . . ?
N2 C10 C15 C14 -176.35(18) . . . . ?
N2 C10 C11 C12 175.22(18) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C14 C15 C10 C11 0.3(2) . . . . ?
C14 C13 C12 C11 0.6(2) . . . . ?
C15 C10 C11 C12 -1.4(2) . . . . ?


_olex2_exptl_crystal_mounting_method -
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.751
_chemical_name_common            
3-(4-bromophenyl)-4-phenyl-4H-1,2,4-oxadiazin-5(6H)-one
####################################################################### 
# 
# 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_UBJ-988
_database_code_depnum_ccdc_archive 'CCDC 2404213'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-03-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        
3-(4-(trifluoromethyl)phenyl)-4H-1,2,4-oxadiazin-5(6H)-one
_chemical_formula_moiety         'C10 H7 F3 N2 O2'
_chemical_formula_sum            'C10 H7 F3 N2 O2'
_chemical_formula_weight         244.174
_chemical_oxdiff_formula         'C10 H7 F3 N2 O2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

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

_symmetry_Int_Tables_number      2
_cell_length_a                   8.2385(3)
_cell_length_b                   11.3733(3)
_cell_length_c                   12.0528(4)
_cell_angle_alpha                116.505(3)
_cell_angle_beta                 94.639(3)
_cell_angle_gamma                100.632(3)
_cell_volume                     976.03(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7188
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.2680
_cell_measurement_theta_min      4.4810
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_description       prism
_exptl_crystal_F_000             498.355
_exptl_crystal_preparation       -
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.9949
_diffrn_reflns_Laue_measured_fraction_max 0.9387
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12441
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9387
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         80.01
_diffrn_reflns_theta_min         4.17
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9949
_diffrn_measured_fraction_theta_max 0.9387
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  72.00   0.50    0.15    --   47.38  77.00 -60.00   92
  2  ω     77.00 120.00   0.50    0.15    --   47.38  77.00 -60.00   86
  3  ω     99.00 130.00   0.50    0.60    --  113.25  61.00-150.00   62
  4  ω    139.00 177.00   0.50    0.60    --  113.25  61.00-150.00   76
  5  ω    121.00 172.00   0.50    0.60    --  113.25  30.00-120.00  102
  6  ω     92.00 178.00   0.50    0.60    --  113.25  77.00 120.00  172
  7  ω     56.00  81.00   0.50    0.60    --  113.25 -94.00-120.00   50
  8  ω     79.00 120.00   0.50    0.60    --  113.25-140.00-105.00   82
  9  ω     59.00 103.00   0.50    0.15    --   47.38-140.00-105.00   88
 10  ω     42.00  80.00   0.50    0.60    --  113.25-125.00 -30.00   76
 11  ω     83.00 109.00   0.50    0.60    --  113.25-125.00 -30.00   52
 12  ω     45.00  96.00   0.50    0.60    --  113.25-125.00   0.00  102
 13  ω     41.00  89.00   0.50    0.15    --   47.38-129.00  68.00   96
 14  ω     43.00 106.00   0.50    0.60    --  113.25-125.00 150.00  126
 15  ω     42.00 101.00   0.50    0.60    --  113.25-125.00 120.00  118
 16  ω     73.00  99.00   0.50    0.60    --  113.25-129.00  68.00   52
 17  ω     42.00  84.00   0.50    0.60    --  113.25 -77.00  30.00   84
 18  ω     45.00  71.00   0.50    0.60    --  113.25 -61.00  60.00   52
 19  ω     79.00 106.00   0.50    0.60    --  113.25 -77.00  90.00   54
 20  ω     45.00  70.00   0.50    0.60    --  113.25 -61.00 -60.00   50
 21  ω     42.00  67.00   0.50    0.60    --  113.25 -61.00 -90.00   50
 22  ω     43.00  70.00   0.50    0.60    --  113.25 -61.00-120.00   54
 23  ω     42.00  68.00   0.50    0.60    --  113.25 -61.00-150.00   52
 24  ω     95.00 129.00   0.50    0.60    --  113.25 140.00 -45.00   68
 25  ω     71.00  96.00   0.50    0.15    --   47.38 129.00 140.00   50
 26  ω     73.00  98.00   0.50    0.60    --  113.25 129.00 140.00   50
 27  ω    101.00 139.00   0.50    0.60    --  113.25 129.00 140.00   76
 28  ω     73.00 106.00   0.50    0.15    --   47.38 140.00 -45.00   66
 29  ω     75.00 119.00   0.50    0.15    --   47.38 125.00-180.00   88
 30  ω    -26.00  28.00   0.50    0.15    --  -47.38  19.00 -90.00  108
 31  ω    -25.00  20.00   0.50    0.15    --  -47.38  19.00 -30.00   90
 32  ω    -23.00  28.00   0.50    0.15    --  -47.38  19.00-180.00  102
 33  ω    -71.00 -42.00   0.50    0.60    -- -106.00  61.00-150.00   58
 34  ω    -71.00 -46.00   0.50    0.60    -- -106.00  61.00 -30.00   50
 35  ω   -108.00 -66.00   0.50    0.60    -- -106.00 110.00  36.79   84
 36  ω   -122.00 -93.00   0.50    0.60    -- -106.00 140.00 -45.00   58
 37  ω    -84.00 -34.00   0.50    0.60    -- -106.00 125.00-180.00  100
 38  ω    -73.00 -46.00   0.50    0.60    -- -106.00 125.00-120.00   54
 39  ω   -111.00 -82.00   0.50    0.60    -- -106.00 125.00-120.00   58
 40  ω    -86.00 -61.00   0.50    0.15    --  -47.38 140.00 -45.00   50
 41  ω   -115.00 -33.00   0.50    0.60    -- -106.00 129.00 140.00  164
 42  ω    -78.00 -52.00   0.50    0.15    --  -47.38 129.00 140.00   52
 43  ω   -118.00 -93.00   0.50    0.60    -- -106.00 -15.00 120.00   50
 44  ω   -176.00-129.00   0.50    0.60    -- -106.00 -15.00 120.00   94
 45  ω   -127.00-102.00   0.50    0.60    -- -106.00 -30.00 -30.00   50
 46  ω   -174.00-106.00   0.50    0.60    -- -106.00 -61.00 -90.00  136
 47  ω   -172.00-147.00   0.50    0.60    -- -106.00 -30.00 -30.00   50
 48  ω   -143.00 -92.00   0.50    0.60    -- -106.00-125.00  30.00  102
 49  ω   -111.00 -73.00   0.50    0.15    --  -47.38-129.00  68.00   76
 50  ω   -116.00 -90.00   0.50    0.15    --  -47.38-140.00-105.00   52
 51  ω   -149.00 -64.00   0.50    0.60    -- -106.00-140.00-105.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0168523000
_diffrn_orient_matrix_UB_12      0.1501609000
_diffrn_orient_matrix_UB_13      0.0350677000
_diffrn_orient_matrix_UB_21      -0.0402849000
_diffrn_orient_matrix_UB_22      -0.0391878000
_diffrn_orient_matrix_UB_23      -0.1409519000
_diffrn_orient_matrix_UB_31      -0.1886366000
_diffrn_orient_matrix_UB_32      -0.0178720000
_diffrn_orient_matrix_UB_33      0.0055473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          -
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3459
_reflns_number_total             4010
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5013
_refine_diff_density_min         -0.5385
_refine_diff_density_rms         0.1128
_refine_ls_d_res_high            0.7828
_refine_ls_d_res_low             10.5987
_refine_ls_goodness_of_fit_ref   1.0471
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.0471
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+0.5690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1480
_refine_special_details          -
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.49450(16) 0.38365(13) 0.52584(11) 0.0339(3) Uani 1.000000 .
F3a F 0.32668(16) 0.83176(14) 0.54351(12) 0.0366(3) Uani 1.000000 .
F2 F 0.24334(16) 0.38363(13) 0.56024(11) 0.0331(3) Uani 1.000000 .
F3 F 0.30393(17) 0.19568(12) 0.44341(10) 0.0340(3) Uani 1.000000 .
F1a F 0.13696(19) 0.64580(14) 0.48078(13) 0.0407(3) Uani 1.000000 .
F2a F 0.07077(18) 0.83806(15) 0.56114(11) 0.0397(3) Uani 1.000000 .
C5a C 0.0499(2) 0.76123(19) 0.12919(18) 0.0222(4) Uani 1.000000 .
C3a C 0.0192(3) 0.6477(2) 0.25751(19) 0.0253(4) Uani 1.000000 .
C2a C 0.1316(3) 0.7595(2) 0.35719(18) 0.0241(4) Uani 1.000000 .
C6 C 0.3518(3) 0.1786(2) 0.78385(18) 0.0247(4) Uani 1.000000 .
C5 C 0.4847(2) 0.27375(19) 0.88008(17) 0.0211(4) Uani 1.000000 .
C2 C 0.4067(2) 0.29793(19) 0.66311(17) 0.0234(4) Uani 1.000000 .
C1 C 0.3629(3) 0.3147(2) 0.54869(18) 0.0257(4) Uani 1.000000 .
C1a C 0.1669(3) 0.7677(2) 0.4843(2) 0.0302(4) Uani 1.000000 .
C7 C 0.3129(3) 0.1915(2) 0.67604(18) 0.0251(4) Uani 1.000000 .
C6a C 0.1643(3) 0.8715(2) 0.22917(19) 0.0288(4) Uani 1.000000 .
C7a C 0.2057(3) 0.8701(2) 0.34233(18) 0.0286(4) Uani 1.000000 .
C8 C 0.5346(2) 0.26421(18) 0.99641(17) 0.0213(4) Uani 1.000000 .
C10a C 0.0761(2) 0.85235(19) -0.13013(18) 0.0238(4) Uani 1.000000 .
C4 C 0.5762(3) 0.3811(2) 0.86625(18) 0.0246(4) Uani 1.000000 .
O1a O -0.18983(17) 0.69407(15) -0.17063(13) 0.0276(3) Uani 1.000000 .
O2a O 0.16684(19) 0.93111(15) -0.15568(13) 0.0310(3) Uani 1.000000 .
N2 N 0.4444(2) 0.15869(16) 1.01338(15) 0.0231(3) Uani 1.000000 .
C4a C -0.0199(3) 0.64883(19) 0.14422(18) 0.0241(4) Uani 1.000000 .
C8a C -0.0041(2) 0.76422(19) 0.01021(17) 0.0217(4) Uani 1.000000 .
O2 O 0.3734(2) 0.07763(15) 1.14876(13) 0.0309(3) Uani 1.000000 .
O1 O 0.71219(17) 0.33497(15) 1.18150(12) 0.0261(3) Uani 1.000000 .
N1 N 0.6642(2) 0.35350(17) 1.07560(15) 0.0245(4) Uani 1.000000 .
N1a N -0.1379(2) 0.67705(18) -0.06397(15) 0.0258(4) Uani 1.000000 .
C3 C 0.5390(3) 0.39272(19) 0.75847(19) 0.0252(4) Uani 1.000000 .
N2a N 0.0883(2) 0.86426(17) -0.01255(15) 0.0234(3) Uani 1.000000 .
C10 C 0.4549(2) 0.16479(19) 1.12858(17) 0.0238(4) Uani 1.000000 .
C9 C 0.5750(2) 0.2909(2) 1.23056(17) 0.0237(4) Uani 1.000000 .
C9a C -0.0570(3) 0.7308(2) -0.22694(18) 0.0249(4) Uani 1.000000 .
H9a H 0.514(3) 0.365(2) 1.270(2) 0.022(5) Uiso 1.000000 .
H9b H 0.624(3) 0.275(3) 1.296(2) 0.025(6) Uiso 1.000000 .
H9aa H -0.109(3) 0.752(3) -0.289(2) 0.033(7) Uiso 1.000000 .
H4 H 0.666(3) 0.446(3) 0.931(2) 0.027(6) Uiso 1.000000 .
H9ab H -0.001(3) 0.657(3) -0.271(2) 0.022(5) Uiso 1.000000 .
H2 H 0.369(4) 0.091(3) 0.955(3) 0.037(7) Uiso 1.000000 .
H6a H 0.213(4) 0.946(3) 0.219(3) 0.044(8) Uiso 1.000000 .
H4a H -0.097(3) 0.573(3) 0.075(3) 0.035(7) Uiso 1.000000 .
H7 H 0.219(3) 0.127(3) 0.610(2) 0.032(6) Uiso 1.000000 .
H3a H -0.032(4) 0.570(3) 0.272(3) 0.041(7) Uiso 1.000000 .
H7a H 0.283(3) 0.944(3) 0.409(3) 0.032(6) Uiso 1.000000 .
H2a H 0.171(4) 0.927(3) 0.044(3) 0.042(8) Uiso 1.000000 .
H6 H 0.287(4) 0.107(3) 0.790(2) 0.035(7) Uiso 1.000000 .
H3 H 0.609(4) 0.465(3) 0.749(2) 0.037(7) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.339(2) . ?
F3a C1a 1.343(3) . ?
F2 C1 1.347(2) . ?
F3 C1 1.343(2) . ?
F1a C1a 1.343(2) . ?
F2a C1a 1.348(3) . ?
C5a C6a 1.395(3) . ?
C5a C4a 1.396(3) . ?
C5a C8a 1.484(3) . ?
C3a C2a 1.393(3) . ?
C3a C4a 1.383(3) . ?
C3a H3a 1.00(3) . ?
C2a C1a 1.493(3) . ?
C2a C7a 1.387(3) . ?
C6 C5 1.398(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.92(3) . ?
C5 C8 1.485(2) . ?
C5 C4 1.396(3) . ?
C2 C1 1.499(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.389(3) . ?
C7 H7 0.97(3) . ?
C6a C7a 1.387(3) . ?
C6a H6a 0.93(3) . ?
C7a H7a 0.93(3) . ?
C8 N2 1.396(2) . ?
C8 N1 1.286(3) . ?
C10a O2a 1.222(2) . ?
C10a N2a 1.355(2) . ?
C10a C9a 1.506(3) . ?
C4 C3 1.380(3) . ?
C4 H4 0.95(3) . ?
O1a N1a 1.427(2) . ?
O1a C9a 1.428(2) . ?
N2 C10 1.354(2) . ?
N2 H2 0.86(3) . ?
C4a H4a 0.96(3) . ?
C8a N1a 1.282(3) . ?
C8a N2a 1.393(2) . ?
O2 C10 1.220(2) . ?
O1 N1 1.421(2) . ?
O1 C9 1.429(2) . ?
C3 H3 0.97(3) . ?
N2a H2a 0.87(3) . ?
C10 C9 1.501(3) . ?
C9 H9a 1.02(2) . ?
C9 H9b 0.96(3) . ?
C9a H9aa 0.97(3) . ?
C9a H9ab 0.99(2) . ?

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
C4a C5a C6a 118.99(17) . . ?
C8a C5a C6a 121.14(17) . . ?
C8a C5a C4a 119.81(17) . . ?
C4a C3a C2a 119.49(18) . . ?
H3a C3a C2a 117.9(16) . . ?
H3a C3a C4a 122.6(16) . . ?
C1a C2a C3a 121.36(17) . . ?
C7a C2a C3a 120.22(17) . . ?
C7a C2a C1a 118.30(18) . . ?
C7 C6 C5 119.87(18) . . ?
H6 C6 C5 121.7(17) . . ?
H6 C6 C7 118.4(17) . . ?
C8 C5 C6 122.49(17) . . ?
C4 C5 C6 119.10(17) . . ?
C4 C5 C8 118.40(17) . . ?
C7 C2 C1 120.59(17) . . ?
C3 C2 C1 119.28(17) . . ?
C3 C2 C7 120.09(17) . . ?
F2 C1 F1 105.82(16) . . ?
F3 C1 F1 106.80(15) . . ?
F3 C1 F2 106.12(16) . . ?
C2 C1 F1 112.60(16) . . ?
C2 C1 F2 112.24(16) . . ?
C2 C1 F3 112.74(16) . . ?
F1a C1a F3a 106.78(17) . . ?
F2a C1a F3a 105.86(17) . . ?
F2a C1a F1a 106.54(17) . . ?
C2a C1a F3a 112.73(17) . . ?
C2a C1a F1a 113.32(17) . . ?
C2a C1a F2a 111.12(17) . . ?
C2 C7 C6 120.24(18) . . ?
H7 C7 C6 120.0(16) . . ?
H7 C7 C2 119.8(16) . . ?
C7a C6a C5a 120.31(18) . . ?
H6a C6a C5a 119.1(18) . . ?
H6a C6a C7a 120.5(18) . . ?
C6a C7a C2a 120.07(19) . . ?
H7a C7a C2a 119.7(17) . . ?
H7a C7a C6a 120.2(17) . . ?
N2 C8 C5 119.66(16) . . ?
N1 C8 C5 117.08(16) . . ?
N1 C8 N2 123.23(17) . . ?
N2a C10a O2a 123.18(18) . . ?
C9a C10a O2a 123.17(17) . . ?
C9a C10a N2a 113.63(16) . . ?
C3 C4 C5 120.97(18) . . ?
H4 C4 C5 119.7(16) . . ?
H4 C4 C3 119.3(16) . . ?
C9a O1a N1a 115.21(14) . . ?
C10 N2 C8 121.38(16) . . ?
H2 N2 C8 123.7(19) . . ?
H2 N2 C10 114.5(19) . . ?
C3a C4a C5a 120.88(18) . . ?
H4a C4a C5a 118.6(17) . . ?
H4a C4a C3a 120.6(17) . . ?
N1a C8a C5a 117.66(16) . . ?
N2a C8a C5a 118.71(17) . . ?
N2a C8a N1a 123.57(17) . . ?
C9 O1 N1 114.61(14) . . ?
O1 N1 C8 114.73(15) . . ?
C8a N1a O1a 114.30(15) . . ?
C4 C3 C2 119.71(18) . . ?
H3 C3 C2 121.0(16) . . ?
H3 C3 C4 119.2(16) . . ?
C8a N2a C10a 121.48(17) . . ?
H2a N2a C10a 117(2) . . ?
H2a N2a C8a 120(2) . . ?
O2 C10 N2 123.66(18) . . ?
C9 C10 N2 113.51(16) . . ?
C9 C10 O2 122.83(17) . . ?
C10 C9 O1 110.69(15) . . ?
H9a C9 O1 110.3(13) . . ?
H9a C9 C10 110.0(13) . . ?
H9b C9 O1 105.9(15) . . ?
H9b C9 C10 111.6(15) . . ?
H9b C9 H9a 108.3(19) . . ?
O1a C9a C10a 111.26(15) . . ?
H9aa C9a C10a 110.3(16) . . ?
H9aa C9a O1a 105.8(16) . . ?
H9ab C9a C10a 107.8(14) . . ?
H9ab C9a O1a 113.4(14) . . ?
H9ab C9a H9aa 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C7 -155.66(16) . . . . ?
F1 C1 C2 C3 26.5(2) . . . . ?
F3a C1a C2a C3a 145.72(17) . . . . ?
F3a C1a C2a C7a -38.3(2) . . . . ?
F2 C1 C2 C7 85.05(18) . . . . ?
F2 C1 C2 C3 -92.79(18) . . . . ?
F3 C1 C2 C7 -34.7(2) . . . . ?
F3 C1 C2 C3 147.43(17) . . . . ?
F1a C1a C2a C3a 24.3(2) . . . . ?
F1a C1a C2a C7a -159.73(18) . . . . ?
F2a C1a C2a C3a -95.64(19) . . . . ?
F2a C1a C2a C7a 80.35(19) . . . . ?
C5a C6a C7a C2a -0.8(3) . . . . ?
C5a C4a C3a C2a -0.9(2) . . . . ?
C5a C8a N1a O1a 174.67(16) . . . . ?
C5a C8a N2a C10a 161.86(17) . . . . ?
C3a C2a C7a C6a 1.9(2) . . . . ?
C6 C5 C8 N2 -1.5(2) . . . . ?
C6 C5 C8 N1 176.49(19) . . . . ?
C6 C5 C4 C3 -1.2(2) . . . . ?
C6 C7 C2 C1 -178.45(18) . . . . ?
C6 C7 C2 C3 -0.6(2) . . . . ?
C5 C8 N2 C10 -162.36(17) . . . . ?
C5 C8 N1 O1 -176.48(15) . . . . ?
C5 C4 C3 C2 1.2(2) . . . . ?
C8 N2 C10 O2 176.94(18) . . . . ?
C8 N2 C10 C9 -2.0(2) . . . . ?
C8 N1 O1 C9 -38.96(19) . . . . ?
C10a N2a C8a N1a -21.0(2) . . . . ?
C10a C9a O1a N1a -51.95(18) . . . . ?
O1a N1a C8a N2a -2.53(19) . . . . ?
N2 C10 C9 O1 -32.60(18) . . . . ?
O2 C10 C9 O1 148.4(2) . . . . ?


_olex2_exptl_crystal_mounting_method -
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.332
