# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_bb-rs-isopropanol_oxin_auto
_database_code_depnum_ccdc_archive 'CCDC 2354252'
loop_
_audit_author_name
_audit_author_address
'Bidraha Bagh'
;National Institute of Science Education and Research (NISER), Bhubaneswar
India
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 N O'
_chemical_formula_sum            'C11 H13 N O'
_chemical_formula_weight         175.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/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'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   21.3851(7)
_cell_length_b                   5.29270(10)
_cell_length_c                   18.3278(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.340(4)
_cell_angle_gamma                90
_cell_volume                     1932.20(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5004
_cell_measurement_temperature    297.46(10)
_cell_measurement_theta_max      75.2290
_cell_measurement_theta_min      4.4010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.471
_diffrn_reflns_theta_min         4.439
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -28.00   0.50    0.44    --  -38.50 -55.00 -17.00  146
  2  ω    -49.00  25.00   0.50    0.44    --  -38.50  55.00 125.00  148
  3  ω     39.00 112.00   0.50    0.44    --   49.06  55.00 125.00  146
  4  ω    -14.00  60.00   0.50    0.44    --   49.06 -55.00 -17.00  148
  5  ω     92.00 165.00   0.50    1.49    --  102.00  55.00 125.00  146
  6  ω     39.00 113.00   0.50    1.49    --  102.00 -55.00 -17.00  148
  7  ω    -42.00  28.00   0.50    0.44    --  -38.50  38.00 -90.00  140
  8  ω    -50.00  24.00   0.50    0.44    --  -38.50  57.00-180.00  148
  9  ω    103.00 167.00   0.50    1.49    --  102.00  77.00  30.00  128
 10  ω    103.00 167.00   0.50    1.49    --  102.00  77.00  60.00  128
 11  ω     97.00 165.00   0.50    1.49    --  102.00 125.00   0.00  136
 12  ω    103.00 167.00   0.50    1.49    --  102.00  77.00-120.00  128
 13  ω     99.00 170.00   0.50    1.49    --  102.00  30.00  30.00  142
 14  ω     98.00 167.00   0.50    1.49    --  102.00  45.00   0.00  138
 15  ω     38.00 107.00   0.50    1.49    --  102.00 -45.00 120.00  138
 16  ω     97.00 165.00   0.50    1.49    --  102.00 125.00-120.00  136
 17  ω     34.00 105.00   0.50    1.49    --  102.00 -30.00 120.00  142
 18  ω     97.00 165.00   0.50    1.49    --  102.00 125.00 120.00  136
 19  ω     38.00 112.00   0.50    0.44    --   49.06  57.00 -90.00  148
 20  ω     38.00 112.00   0.50    0.44    --   49.06  57.00-150.00  148
 21  ω     38.00 112.00   0.50    0.44    --   49.06  57.00  60.00  148
 22  ω     38.00 112.00   0.50    0.44    --   49.06  57.00-180.00  148
 23  ω     38.00 112.00   0.50    0.44    --   49.06  57.00 -30.00  148
 24  ω     98.00 154.00   0.50    1.49    --  102.00  45.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1660
_reflns_number_total             1973
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.055
_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)+(0.0596P)²+0.4735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1157
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45131(5) 0.2111(2) 0.42280(6) 0.0648(3) Uani 1 1 d . . . . .
N1 N 0.45380(5) 0.1951(2) 0.54861(6) 0.0504(3) Uani 1 1 d . . . . .
H1 H 0.479485 0.065427 0.564058 0.060 Uiso 1 1 calc R U . . .
C7 C 0.38774(6) 0.5270(2) 0.55259(7) 0.0420(3) Uani 1 1 d . . . . .
C8 C 0.38800(6) 0.5159(2) 0.47076(7) 0.0427(3) Uani 1 1 d . . . . .
H8 H 0.408923 0.669959 0.460627 0.051 Uiso 1 1 calc R U . . .
C2 C 0.42715(6) 0.3308(2) 0.59638(7) 0.0445(3) Uani 1 1 d . . . . .
C9 C 0.31792(6) 0.4849(2) 0.40592(7) 0.0466(3) Uani 1 1 d . . . . .
H9 H 0.288839 0.614614 0.414957 0.056 Uiso 1 1 calc R U . . .
C1 C 0.43436(6) 0.2921(2) 0.47548(7) 0.0475(3) Uani 1 1 d . . . . .
C6 C 0.35643(7) 0.6893(2) 0.58723(8) 0.0505(3) Uani 1 1 d . . . . .
H6 H 0.329884 0.820840 0.558646 0.061 Uiso 1 1 calc R U . . .
C3 C 0.43592(7) 0.2914(3) 0.67379(8) 0.0552(3) Uani 1 1 d . . . . .
H3 H 0.462097 0.158840 0.702231 0.066 Uiso 1 1 calc R U . . .
C4 C 0.40403(7) 0.4580(3) 0.70774(8) 0.0581(4) Uani 1 1 d . . . . .
H4 H 0.409102 0.436712 0.759964 0.070 Uiso 1 1 calc R U . . .
C5 C 0.36505(8) 0.6540(3) 0.66541(8) 0.0574(4) Uani 1 1 d . . . . .
H5 H 0.344376 0.763356 0.689384 0.069 Uiso 1 1 calc R U . . .
C11 C 0.28687(8) 0.2310(3) 0.41063(9) 0.0636(4) Uani 1 1 d . . . . .
H11A H 0.311293 0.099819 0.396440 0.095 Uiso 1 1 calc R U . . .
H11B H 0.240935 0.229072 0.375284 0.095 Uiso 1 1 calc R U . . .
H11C H 0.288712 0.203397 0.463136 0.095 Uiso 1 1 calc R U . . .
C10 C 0.31973(9) 0.5319(3) 0.32530(9) 0.0724(5) Uani 1 1 d . . . . .
H10A H 0.337953 0.696738 0.323749 0.109 Uiso 1 1 calc R U . . .
H10B H 0.275014 0.522347 0.286974 0.109 Uiso 1 1 calc R U . . .
H10C H 0.347372 0.406541 0.314018 0.109 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 C1 1.2256(15) . ?
N1 H1 0.8600 . ?
N1 C2 1.4036(16) . ?
N1 C1 1.3519(17) . ?
C7 C8 1.5028(16) . ?
C7 C2 1.3929(17) . ?
C7 C6 1.3782(17) . ?
C8 H8 0.9800 . ?
C8 C9 1.5455(17) . ?
C8 C1 1.5267(16) . ?
C2 C3 1.3777(18) . ?
C9 H9 0.9800 . ?
C9 C11 1.515(2) . ?
C9 C10 1.5127(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.3891(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 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 . ?

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 H1 124.0 . . ?
C1 N1 H1 124.0 . . ?
C1 N1 C2 112.08(11) . . ?
C2 C7 C8 108.95(10) . . ?
C6 C7 C8 131.52(11) . . ?
C6 C7 C2 119.53(12) . . ?
C7 C8 H8 108.9 . . ?
C7 C8 C9 114.64(10) . . ?
C7 C8 C1 102.24(9) . . ?
C9 C8 H8 108.9 . . ?
C1 C8 H8 108.9 . . ?
C1 C8 C9 112.91(10) . . ?
C7 C2 N1 108.66(11) . . ?
C3 C2 N1 129.12(12) . . ?
C3 C2 C7 122.22(12) . . ?
C8 C9 H9 107.1 . . ?
C11 C9 C8 111.88(10) . . ?
C11 C9 H9 107.1 . . ?
C10 C9 C8 111.80(11) . . ?
C10 C9 H9 107.1 . . ?
C10 C9 C11 111.65(12) . . ?
O1 C1 N1 125.16(12) . . ?
O1 C1 C8 126.79(12) . . ?
N1 C1 C8 108.05(10) . . ?
C7 C6 H6 120.4 . . ?
C7 C6 C5 119.14(13) . . ?
C5 C6 H6 120.4 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.33(13) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.26(12) . . ?
C5 C4 H4 119.4 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(13) . . ?
C4 C5 H5 119.7 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
N1 C2 C3 C4 179.19(13) . . . . ?
C7 C8 C9 C11 -66.36(14) . . . . ?
C7 C8 C9 C10 167.57(11) . . . . ?
C7 C8 C1 O1 -178.59(14) . . . . ?
C7 C8 C1 N1 1.72(13) . . . . ?
C7 C2 C3 C4 -0.51(19) . . . . ?
C7 C6 C5 C4 -0.5(2) . . . . ?
C8 C7 C2 N1 0.85(13) . . . . ?
C8 C7 C2 C3 -179.40(11) . . . . ?
C8 C7 C6 C5 179.82(12) . . . . ?
C2 N1 C1 O1 178.96(13) . . . . ?
C2 N1 C1 C8 -1.34(15) . . . . ?
C2 C7 C8 C9 121.00(11) . . . . ?
C2 C7 C8 C1 -1.53(12) . . . . ?
C2 C7 C6 C5 0.17(18) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C9 C8 C1 O1 57.71(18) . . . . ?
C9 C8 C1 N1 -121.98(12) . . . . ?
C1 N1 C2 C7 0.33(15) . . . . ?
C1 N1 C2 C3 -179.40(13) . . . . ?
C1 C8 C9 C11 50.20(14) . . . . ?
C1 C8 C9 C10 -75.88(14) . . . . ?
C6 C7 C8 C9 -58.69(17) . . . . ?
C6 C7 C8 C1 178.78(13) . . . . ?
C6 C7 C2 N1 -179.43(11) . . . . ?
C6 C7 C2 C3 0.33(19) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?

_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_bb-rs-p3-182_auto
_database_code_depnum_ccdc_archive 'CCDC 2354253'
loop_
_audit_author_name
_audit_author_address
'Bidraha Bagh'
;National Institute of Science Education and Research (NISER), Bhubaneswar
India
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-05-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 Cl N O'
_chemical_formula_sum            'C13 H14 Cl N O'
_chemical_formula_weight         235.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9223(2)
_cell_length_b                   5.97560(10)
_cell_length_c                   18.2274(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.405(2)
_cell_angle_gamma                90
_cell_volume                     1157.24(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5879
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9370
_cell_measurement_theta_min      4.3170
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.611
_exptl_absorpt_coefficient_mu    2.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.374
_diffrn_reflns_theta_min         4.327
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  15.00   0.50    0.17    --  -38.50 100.00  14.00  178
  2  ω     35.00 107.00   0.50    1.14    --  102.00-100.00 -90.00  144
  3  ω    104.00 170.00   0.50    1.14    --  102.00 100.00  14.00  132
  4  ω   -101.00 -27.00   0.50    0.17    --  -38.50 -57.00 150.00  148
  5  ω   -108.00 -33.00   0.50    0.17    --  -38.50 -19.00-150.00  150
  6  ω     46.00 115.00   0.50    0.17    --   48.81  38.00  30.00  138
  7  ω     37.00 112.00   0.50    0.17    --   48.81  57.00  30.00  150
  8  ω      7.00  84.00   0.50    0.17    --   48.81-100.00 -90.00  154
  9  ω     98.00 167.00   0.50    1.14    --  102.00  45.00  90.00  138
 10  ω     39.00 115.00   0.50    1.14    --  102.00 -61.00-120.00  152
 11  ω     94.00 171.00   0.50    1.14    --  102.00  15.00  90.00  154
 12  ω     34.00 105.00   0.50    1.14    --  102.00 -30.00 -60.00  142
 13  ω     89.00 165.00   0.50    1.14    --  102.00  61.00 -60.00  152
 14  ω     34.00 110.00   0.50    1.14    --  102.00 -15.00 -90.00  152
 15  ω     34.00 105.00   0.50    1.14    --  102.00 -30.00 120.00  142
 16  ω    103.00 167.00   0.50    1.14    --  102.00  77.00 -90.00  128
 17  ω     97.00 165.00   0.50    1.14    --  102.00 125.00 120.00  136
 18  ω     42.00  99.00   0.50    1.14    --  102.00 -45.00  60.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661009000
_diffrn_orient_matrix_UB_12      -0.0274972000
_diffrn_orient_matrix_UB_13      -0.0654654000
_diffrn_orient_matrix_UB_21      0.1233945000
_diffrn_orient_matrix_UB_22      0.0883952000
_diffrn_orient_matrix_UB_23      0.0507644000
_diffrn_orient_matrix_UB_31      0.0377427000
_diffrn_orient_matrix_UB_32      -0.2406773000
_diffrn_orient_matrix_UB_33      0.0261943000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2173
_reflns_number_total             2344
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.068
_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)+(0.0565P)²+0.4874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1017
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27340(3) 0.18141(6) 0.43361(2) 0.02024(14) Uani 1 1 d . . . . .
O1 O 0.70774(9) 0.57562(18) 0.78428(6) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.60490(11) 0.3950(2) 0.67733(7) 0.0165(3) Uani 1 1 d . . . . .
H1 H 0.653171 0.275415 0.682342 0.020 Uiso 1 1 calc R U . . .
C8 C 0.49931(13) 0.4280(2) 0.61801(8) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.44921(13) 0.2834(3) 0.55962(8) 0.0166(3) Uani 1 1 d . . . . .
H7 H 0.486068 0.141797 0.554730 0.020 Uiso 1 1 calc R U . . .
C3 C 0.44675(13) 0.6373(3) 0.62657(8) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.28704(13) 0.5644(3) 0.51403(8) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.214322 0.609735 0.477496 0.021 Uiso 1 1 calc R U . . .
C6 C 0.34148(13) 0.3571(3) 0.50826(8) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.62373(13) 0.5698(2) 0.72613(8) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.34029(13) 0.7061(3) 0.57420(8) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.303718 0.847942 0.579033 0.021 Uiso 1 1 calc R U . . .
C2 C 0.52474(12) 0.7491(3) 0.69595(8) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.568277 0.880637 0.679521 0.019 Uiso 1 1 calc R U . . .
C9 C 0.45071(14) 0.8310(3) 0.75272(8) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.379788 0.925822 0.724560 0.023 Uiso 1 1 calc R U . . .
C10 C 0.52575(14) 0.9712(3) 0.81823(9) 0.0229(3) Uani 1 1 d . . . . .
H10A H 0.606487 0.897943 0.842014 0.027 Uiso 1 1 calc R U . . .
H10B H 0.543034 1.122722 0.801082 0.027 Uiso 1 1 calc R U . . .
C11 C 0.43826(16) 0.9817(3) 0.87268(9) 0.0290(4) Uani 1 1 d . . . . .
H11A H 0.378675 1.108314 0.859830 0.035 Uiso 1 1 calc R U . . .
H11B H 0.487354 1.000341 0.925258 0.035 Uiso 1 1 calc R U . . .
C13 C 0.39367(17) 0.6456(3) 0.79278(10) 0.0298(4) Uani 1 1 d . . . . .
H13A H 0.314946 0.587820 0.759808 0.036 Uiso 1 1 calc R U . . .
H13B H 0.453619 0.519986 0.806905 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3672(2) 0.7570(4) 0.86316(11) 0.0392(5) Uani 1 1 d . . . . .
H12A H 0.397322 0.661166 0.908009 0.047 Uiso 1 1 calc R U . . .
H12B H 0.275713 0.782306 0.856737 0.047 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
Cl1 C6 1.7429(15) . ?
O1 C1 1.2311(18) . ?
N1 H1 0.8800 . ?
N1 C8 1.3999(18) . ?
N1 C1 1.356(2) . ?
C8 C7 1.382(2) . ?
C8 C3 1.400(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.394(2) . ?
C3 C4 1.385(2) . ?
C3 C2 1.5070(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C5 C4 1.401(2) . ?
C1 C2 1.5310(19) . ?
C4 H4 0.9500 . ?
C2 H2 1.0000 . ?
C2 C9 1.5338(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.531(2) . ?
C9 C13 1.536(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.530(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.531(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 H1 124.1 . . ?
C1 N1 H1 124.1 . . ?
C1 N1 C8 111.75(12) . . ?
N1 C8 C3 108.99(13) . . ?
C7 C8 N1 127.97(14) . . ?
C7 C8 C3 123.03(13) . . ?
C8 C7 H7 121.9 . . ?
C8 C7 C6 116.20(14) . . ?
C6 C7 H7 121.9 . . ?
C8 C3 C2 108.83(12) . . ?
C4 C3 C8 119.26(14) . . ?
C4 C3 C2 131.92(14) . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.41(13) . . ?
C4 C5 H5 120.3 . . ?
C7 C6 Cl1 118.34(12) . . ?
C5 C6 Cl1 118.94(11) . . ?
C5 C6 C7 122.72(14) . . ?
O1 C1 N1 123.78(14) . . ?
O1 C1 C2 127.79(14) . . ?
N1 C1 C2 108.43(12) . . ?
C3 C4 C5 119.37(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C3 C2 C1 101.90(12) . . ?
C3 C2 H2 108.2 . . ?
C3 C2 C9 115.08(11) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C9 114.83(12) . . ?
C9 C2 H2 108.2 . . ?
C2 C9 H9 107.5 . . ?
C2 C9 C13 115.18(13) . . ?
C10 C9 C2 115.48(12) . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C13 103.11(13) . . ?
C13 C9 H9 107.5 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.07(12) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
C10 C11 C12 105.40(14) . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C9 C13 H13A 110.7 . . ?
C9 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C12 C13 C9 105.11(15) . . ?
C12 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
C13 C12 C11 106.57(14) . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?

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 C1 C2 C3 -176.93(14) . . . . ?
O1 C1 C2 C9 -51.85(19) . . . . ?
N1 C8 C7 C6 179.06(13) . . . . ?
N1 C8 C3 C4 -179.74(12) . . . . ?
N1 C8 C3 C2 0.67(15) . . . . ?
N1 C1 C2 C3 3.10(14) . . . . ?
N1 C1 C2 C9 128.18(13) . . . . ?
C8 N1 C1 O1 177.08(13) . . . . ?
C8 N1 C1 C2 -2.95(15) . . . . ?
C8 C7 C6 Cl1 -179.66(10) . . . . ?
C8 C7 C6 C5 0.7(2) . . . . ?
C8 C3 C4 C5 0.3(2) . . . . ?
C8 C3 C2 C1 -2.23(14) . . . . ?
C8 C3 C2 C9 -127.14(13) . . . . ?
C7 C8 C3 C4 -0.6(2) . . . . ?
C7 C8 C3 C2 179.80(13) . . . . ?
C3 C8 C7 C6 0.1(2) . . . . ?
C3 C2 C9 C10 -172.40(13) . . . . ?
C3 C2 C9 C13 67.49(18) . . . . ?
C6 C5 C4 C3 0.4(2) . . . . ?
C1 N1 C8 C7 -177.60(13) . . . . ?
C1 N1 C8 C3 1.48(16) . . . . ?
C1 C2 C9 C10 69.74(17) . . . . ?
C1 C2 C9 C13 -50.37(18) . . . . ?
C4 C3 C2 C1 178.25(15) . . . . ?
C4 C3 C2 C9 53.3(2) . . . . ?
C4 C5 C6 Cl1 179.40(11) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C2 C3 C4 C5 179.82(13) . . . . ?
C2 C9 C10 C11 -167.78(14) . . . . ?
C2 C9 C13 C12 160.74(14) . . . . ?
C9 C10 C11 C12 32.81(18) . . . . ?
C9 C13 C12 C11 -13.8(2) . . . . ?
C10 C9 C13 C12 34.04(18) . . . . ?
C10 C11 C12 C13 -11.8(2) . . . . ?
C13 C9 C10 C11 -41.27(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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.248
_oxdiff_exptl_absorpt_empirical_full_min 0.591
####################################################################### 
# 
# 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_bb-rs_p3
_database_code_depnum_ccdc_archive 'CCDC 2354254'
loop_
_audit_author_name
_audit_author_address
'Bidraha Bagh'
;National Institute of Science Education and Research (NISER), Bhubaneswar
India
;
_audit_update_record             
;
2024-05-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-01
_audit_creation_method           
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H15 N O2)'
_chemical_formula_sum            'C32 H30 N2 O4'
_chemical_formula_weight         506.58
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.2634(2)
_cell_length_b                   24.2647(7)
_cell_length_c                   14.6681(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.182(2)
_cell_angle_gamma                90
_cell_volume                     2574.60(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6931
_cell_measurement_temperature    100.04(10)
_cell_measurement_theta_max      77.9360
_cell_measurement_theta_min      6.0460
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78355
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10691
_diffrn_reflns_point_group_measured_fraction_full 0.632
_diffrn_reflns_point_group_measured_fraction_max 0.607
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.258
_diffrn_reflns_theta_min         3.532
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.04(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  13.00   0.50    0.20    --  -38.50 103.00  10.00  176
  2  ω      8.00  87.00   0.50    0.20    --   49.56-103.00 -92.00  158
  3  ω    104.00 175.00   0.50    0.92    --  107.46 103.00  10.00  142
  4  ω     40.00 108.00   0.50    0.92    --  107.46-103.00 -92.00  136
  5  ω    -42.00  28.00   0.50    0.20    --  -38.50  37.00-180.00  140
  6  ω    -44.00  31.00   0.50    0.20    --  -38.50  19.00 150.00  150
  7  ω    -42.00  28.00   0.50    0.20    --  -38.50  37.00 -30.00  140
  8  ω    -17.00  53.00   0.50    0.20    --   49.56 -37.00-180.00  140
  9  ω     43.00 112.00   0.50    0.92    --  107.46 -45.00  90.00  138
 10  ω     39.00 107.00   0.50    0.92    --  107.46 -94.00 -60.00  136
 11  ω     45.00 121.00   0.50    0.92    --  107.46 -61.00 -90.00  152
 12  ω     39.00 111.00   0.50    0.92    --  107.46 -30.00-180.00  144
 13  ω    103.00 172.00   0.50    0.92    --  107.46  77.00-180.00  138
 14  ω     45.00 113.00   0.50    0.92    --  107.46-125.00  90.00  136
 15  ω     43.00 112.00   0.50    0.92    --  107.46 -45.00  30.00  138
 16  ω     39.00  98.00   0.50    0.92    --  107.46 -94.00-180.00  118
 17  ω     42.00 104.00   0.50    0.92    --  107.46 -30.00  90.00  124
 18  ω     45.00 120.00   0.50    0.92    --  107.46 -61.00  30.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513273000
_diffrn_orient_matrix_UB_12      -0.0459923000
_diffrn_orient_matrix_UB_13      0.0656080000
_diffrn_orient_matrix_UB_21      0.0304219000
_diffrn_orient_matrix_UB_22      0.0400903000
_diffrn_orient_matrix_UB_23      0.0813146000
_diffrn_orient_matrix_UB_31      -0.2044894000
_diffrn_orient_matrix_UB_32      0.0175220000
_diffrn_orient_matrix_UB_33      -0.0142989000
_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'
_reflns_Friedel_coverage         0.237
_reflns_Friedel_fraction_full    0.262
_reflns_Friedel_fraction_max     0.233
_reflns_number_gt                3043
_reflns_number_total             3351
_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-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.074
_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)+(0.0626P)²+0.2116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1155
_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
2.a Ternary CH refined with riding coordinates:
 C9B(H9B), C9A(H9A)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1B(H1B), C6B(H6B), C12B(H12B), C7B(H7B), C16A(H16A), C6A(H6A),
 C14B(H14B), C15A(H15A), C4B(H4B), C5B(H5B), C7A(H7A), C4A(H4A), C16B(H16B),
 C5A(H5A), C12A(H12A), C13B(H13B), C15B(H15B), C14A(H14A), C13A(H13A)
2.c Idealised Me refined as rotating group:
 C10A(H10D,H10E,H10F), C10B(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2B(H2B), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2B O 1.0871(3) 0.59133(8) 0.42010(14) 0.0252(4) Uani 1 1 d . . . . .
H2B H 1.1389 0.5607 0.4149 0.038 Uiso 1 1 calc R U . . .
O1B O 0.8136(3) 0.49914(8) 0.39079(15) 0.0264(4) Uani 1 1 d . . . . .
O2A O 1.4398(3) 0.58716(8) 0.58099(15) 0.0270(4) Uani 1 1 d . . . . .
H2A H 1.4956 0.5571 0.5904 0.041 Uiso 1 1 calc R U . . .
O1A O 1.1735(3) 0.49926(8) 0.61979(15) 0.0276(4) Uani 1 1 d . . . . .
N1A N 0.9848(3) 0.57544(10) 0.61898(17) 0.0260(5) Uani 1 1 d . . . . .
H1A H 0.8770 0.5587 0.6167 0.031 Uiso 1 1 calc R U . . .
N1B N 0.6246(3) 0.57430(10) 0.40148(17) 0.0250(5) Uani 1 1 d . . . . .
H1B H 0.5237 0.5569 0.4142 0.030 Uiso 1 1 calc R U . . .
C1A C 1.1485(4) 0.54953(12) 0.62458(19) 0.0243(5) Uani 1 1 d . . . . .
C3A C 1.1964(4) 0.64550(12) 0.6277(2) 0.0271(6) Uani 1 1 d . . . . .
C1B C 0.7832(4) 0.54907(11) 0.38611(19) 0.0235(5) Uani 1 1 d . . . . .
C2A C 1.3036(4) 0.59271(12) 0.6430(2) 0.0251(6) Uani 1 1 d . . . . .
C6B C 0.5526(4) 0.72542(13) 0.3988(2) 0.0351(7) Uani 1 1 d . . . . .
H6B H 0.4636 0.7532 0.4073 0.042 Uiso 1 1 calc R U . . .
C11A C 1.2434(4) 0.59189(13) 0.8120(2) 0.0287(6) Uani 1 1 d . . . . .
C8A C 1.0084(4) 0.63303(12) 0.6172(2) 0.0266(6) Uani 1 1 d . . . . .
C12B C 0.7275(5) 0.63720(14) 0.1588(2) 0.0358(7) Uani 1 1 d . . . . .
H12B H 0.7860 0.6703 0.1806 0.043 Uiso 1 1 calc R U . . .
C7B C 0.5052(4) 0.67058(13) 0.4081(2) 0.0306(6) Uani 1 1 d . . . . .
H7B H 0.3855 0.6601 0.4229 0.037 Uiso 1 1 calc R U . . .
C16A C 1.2040(5) 0.64356(15) 0.8473(2) 0.0387(7) Uani 1 1 d . . . . .
H16A H 1.2656 0.6752 0.8269 0.046 Uiso 1 1 calc R U . . .
C8B C 0.6393(4) 0.63178(11) 0.3948(2) 0.0251(5) Uani 1 1 d . . . . .
C6A C 0.9341(5) 0.72747(14) 0.5997(2) 0.0389(7) Uani 1 1 d . . . . .
H6A H 0.8450 0.7561 0.5910 0.047 Uiso 1 1 calc R U . . .
C14B C 0.4881(5) 0.5920(2) 0.0612(2) 0.0496(10) Uani 1 1 d . . . . .
H14B H 0.3856 0.5939 0.0162 0.059 Uiso 1 1 calc R U . . .
C15A C 1.0771(6) 0.6495(2) 0.9111(3) 0.0553(12) Uani 1 1 d . . . . .
H15A H 1.0553 0.6849 0.9355 0.066 Uiso 1 1 calc R U . . .
C4B C 0.8627(4) 0.70065(12) 0.3650(2) 0.0310(6) Uani 1 1 d . . . . .
H4B H 0.9833 0.7110 0.3513 0.037 Uiso 1 1 calc R U . . .
C5B C 0.7284(4) 0.74061(13) 0.3772(3) 0.0364(7) Uani 1 1 d . . . . .
H5B H 0.7574 0.7785 0.3708 0.044 Uiso 1 1 calc R U . . .
C2B C 0.9233(4) 0.59345(11) 0.35987(19) 0.0235(5) Uani 1 1 d . . . . .
C7A C 0.8745(4) 0.67294(14) 0.6032(2) 0.0327(6) Uani 1 1 d . . . . .
H7A H 0.7468 0.6638 0.5963 0.039 Uiso 1 1 calc R U . . .
C3B C 0.8165(4) 0.64578(11) 0.3732(2) 0.0254(6) Uani 1 1 d . . . . .
C4A C 1.2543(4) 0.69945(13) 0.6227(2) 0.0322(6) Uani 1 1 d . . . . .
H4A H 1.3822 0.7083 0.6287 0.039 Uiso 1 1 calc R U . . .
C16B C 0.7035(5) 0.53892(15) 0.1602(2) 0.0351(7) Uani 1 1 d . . . . .
H16B H 0.7451 0.5040 0.1832 0.042 Uiso 1 1 calc R U . . .
C10A C 1.5595(4) 0.61834(15) 0.7674(2) 0.0367(7) Uani 1 1 d . . . . .
H10D H 1.6560 0.6066 0.7290 0.055 Uiso 1 1 calc R U . . .
H10E H 1.6031 0.6131 0.8320 0.055 Uiso 1 1 calc R U . . .
H10F H 1.5311 0.6574 0.7561 0.055 Uiso 1 1 calc R U . . .
C5A C 1.1204(5) 0.74087(14) 0.6087(2) 0.0379(7) Uani 1 1 d . . . . .
H5A H 1.1574 0.7783 0.6052 0.045 Uiso 1 1 calc R U . . .
C9B C 0.9641(4) 0.58200(12) 0.2596(2) 0.0261(6) Uani 1 1 d . . . . .
H9B H 1.0056 0.5428 0.2576 0.031 Uiso 1 1 calc R U . . .
C11B C 0.7942(4) 0.58665(13) 0.1920(2) 0.0282(6) Uani 1 1 d . . . . .
C12A C 1.1458(5) 0.54709(16) 0.8422(2) 0.0384(7) Uani 1 1 d . . . . .
H12A H 1.1691 0.5114 0.8194 0.046 Uiso 1 1 calc R U . . .
C9A C 1.3854(4) 0.58390(12) 0.7442(2) 0.0281(6) Uani 1 1 d . . . . .
H9A H 1.4247 0.5444 0.7491 0.034 Uiso 1 1 calc R U . . .
C10B C 1.1247(4) 0.61699(15) 0.2310(2) 0.0342(7) Uani 1 1 d . . . . .
H10A H 1.0956 0.6561 0.2377 0.051 Uiso 1 1 calc R U . . .
H10B H 1.1439 0.6092 0.1669 0.051 Uiso 1 1 calc R U . . .
H10C H 1.2374 0.6080 0.2700 0.051 Uiso 1 1 calc R U . . .
C13B C 0.5752(5) 0.63970(18) 0.0939(2) 0.0441(8) Uani 1 1 d . . . . .
H13B H 0.5308 0.6745 0.0719 0.053 Uiso 1 1 calc R U . . .
C15B C 0.5520(5) 0.54190(19) 0.0947(2) 0.0467(9) Uani 1 1 d . . . . .
H15B H 0.4923 0.5090 0.0730 0.056 Uiso 1 1 calc R U . . .
C14A C 0.9822(5) 0.6047(3) 0.9399(3) 0.0638(14) Uani 1 1 d . . . . .
H14A H 0.8944 0.6092 0.9836 0.077 Uiso 1 1 calc R U . . .
C13A C 1.0153(5) 0.5535(2) 0.9049(3) 0.0578(12) Uani 1 1 d . . . . .
H13A H 0.9488 0.5224 0.9237 0.069 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
O2B H2B 0.8400 . ?
O2B C2B 1.417(3) . ?
O1B C1B 1.232(3) . ?
O2A H2A 0.8400 . ?
O2A C2A 1.410(3) . ?
O1A C1A 1.236(3) . ?
N1A H1A 0.8800 . ?
N1A C1A 1.341(4) . ?
N1A C8A 1.409(4) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.341(4) . ?
N1B C8B 1.403(4) . ?
C1A C2A 1.545(4) . ?
C3A C2A 1.506(4) . ?
C3A C8A 1.393(4) . ?
C3A C4A 1.379(4) . ?
C1B C2B 1.554(4) . ?
C2A C9A 1.562(4) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.384(5) . ?
C6B C5B 1.393(5) . ?
C11A C16A 1.395(5) . ?
C11A C12A 1.391(5) . ?
C11A C9A 1.510(4) . ?
C8A C7A 1.375(4) . ?
C12B H12B 0.9500 . ?
C12B C11B 1.391(5) . ?
C12B C13B 1.395(5) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.382(4) . ?
C16A H16A 0.9500 . ?
C16A C15A 1.380(5) . ?
C8B C3B 1.395(4) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.395(5) . ?
C6A C5A 1.386(5) . ?
C14B H14B 0.9500 . ?
C14B C13B 1.383(6) . ?
C14B C15B 1.377(7) . ?
C15A H15A 0.9500 . ?
C15A C14A 1.373(8) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.399(5) . ?
C4B C3B 1.381(4) . ?
C5B H5B 0.9500 . ?
C2B C3B 1.510(4) . ?
C2B C9B 1.552(4) . ?
C7A H7A 0.9500 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.401(5) . ?
C16B H16B 0.9500 . ?
C16B C11B 1.392(5) . ?
C16B C15B 1.396(5) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C10A C9A 1.528(4) . ?
C5A H5A 0.9500 . ?
C9B H9B 1.0000 . ?
C9B C11B 1.515(4) . ?
C9B C10B 1.531(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.388(5) . ?
C9A H9A 1.0000 . ?
C10B H10A 0.9800 . ?
C10B H10B 0.9800 . ?
C10B H10C 0.9800 . ?
C13B H13B 0.9500 . ?
C15B H15B 0.9500 . ?
C14A H14A 0.9500 . ?
C14A C13A 1.375(8) . ?
C13A H13A 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
C2B O2B H2B 109.5 . . ?
C2A O2A H2A 109.5 . . ?
C1A N1A H1A 124.5 . . ?
C1A N1A C8A 111.0(2) . . ?
C8A N1A H1A 124.5 . . ?
C1B N1B H1B 124.1 . . ?
C1B N1B C8B 111.7(2) . . ?
C8B N1B H1B 124.1 . . ?
O1A C1A N1A 126.4(3) . . ?
O1A C1A C2A 124.8(2) . . ?
N1A C1A C2A 108.8(2) . . ?
C8A C3A C2A 108.7(2) . . ?
C4A C3A C2A 131.3(3) . . ?
C4A C3A C8A 120.1(3) . . ?
O1B C1B N1B 126.3(3) . . ?
O1B C1B C2B 125.2(2) . . ?
N1B C1B C2B 108.5(2) . . ?
O2A C2A C1A 111.4(2) . . ?
O2A C2A C3A 111.6(2) . . ?
O2A C2A C9A 111.8(2) . . ?
C1A C2A C9A 106.4(2) . . ?
C3A C2A C1A 101.0(2) . . ?
C3A C2A C9A 114.0(2) . . ?
C7B C6B H6B 119.4 . . ?
C7B C6B C5B 121.2(3) . . ?
C5B C6B H6B 119.4 . . ?
C16A C11A C9A 122.3(3) . . ?
C12A C11A C16A 117.2(3) . . ?
C12A C11A C9A 120.5(3) . . ?
C3A C8A N1A 109.5(2) . . ?
C7A C8A N1A 128.0(3) . . ?
C7A C8A C3A 122.5(3) . . ?
C11B C12B H12B 119.7 . . ?
C11B C12B C13B 120.5(3) . . ?
C13B C12B H12B 119.7 . . ?
C6B C7B H7B 121.4 . . ?
C8B C7B C6B 117.1(3) . . ?
C8B C7B H7B 121.4 . . ?
C11A C16A H16A 119.4 . . ?
C15A C16A C11A 121.1(4) . . ?
C15A C16A H16A 119.4 . . ?
C7B C8B N1B 127.5(3) . . ?
C7B C8B C3B 122.9(3) . . ?
C3B C8B N1B 109.6(2) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C5A C6A C7A 121.5(3) . . ?
C13B C14B H14B 120.5 . . ?
C15B C14B H14B 120.5 . . ?
C15B C14B C13B 119.1(3) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A C16A 120.8(4) . . ?
C14A C15A H15A 119.6 . . ?
C5B C4B H4B 120.7 . . ?
C3B C4B H4B 120.7 . . ?
C3B C4B C5B 118.6(3) . . ?
C6B C5B C4B 120.7(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
O2B C2B C1B 110.6(2) . . ?
O2B C2B C3B 111.2(2) . . ?
O2B C2B C9B 111.3(2) . . ?
C3B C2B C1B 101.3(2) . . ?
C3B C2B C9B 114.7(2) . . ?
C9B C2B C1B 107.2(2) . . ?
C8A C7A C6A 117.1(3) . . ?
C8A C7A H7A 121.4 . . ?
C6A C7A H7A 121.4 . . ?
C8B C3B C2B 108.7(2) . . ?
C4B C3B C8B 119.4(3) . . ?
C4B C3B C2B 131.9(3) . . ?
C3A C4A H4A 120.7 . . ?
C3A C4A C5A 118.6(3) . . ?
C5A C4A H4A 120.7 . . ?
C11B C16B H16B 119.7 . . ?
C11B C16B C15B 120.5(3) . . ?
C15B C16B H16B 119.7 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
C6A C5A C4A 120.3(3) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C2B C9B H9B 106.4 . . ?
C11B C9B C2B 113.1(2) . . ?
C11B C9B H9B 106.4 . . ?
C11B C9B C10B 112.0(2) . . ?
C10B C9B C2B 112.1(2) . . ?
C10B C9B H9B 106.4 . . ?
C12B C11B C16B 118.5(3) . . ?
C12B C11B C9B 122.2(3) . . ?
C16B C11B C9B 119.4(3) . . ?
C11A C12A H12A 119.3 . . ?
C13A C12A C11A 121.4(4) . . ?
C13A C12A H12A 119.3 . . ?
C2A C9A H9A 106.4 . . ?
C11A C9A C2A 112.6(2) . . ?
C11A C9A C10A 112.6(3) . . ?
C11A C9A H9A 106.4 . . ?
C10A C9A C2A 111.9(3) . . ?
C10A C9A H9A 106.4 . . ?
C9B C10B H10A 109.5 . . ?
C9B C10B H10B 109.5 . . ?
C9B C10B H10C 109.5 . . ?
H10A C10B H10B 109.5 . . ?
H10A C10B H10C 109.5 . . ?
H10B C10B H10C 109.5 . . ?
C12B C13B H13B 119.7 . . ?
C14B C13B C12B 120.7(4) . . ?
C14B C13B H13B 119.7 . . ?
C14B C15B C16B 120.7(4) . . ?
C14B C15B H15B 119.6 . . ?
C16B C15B H15B 119.6 . . ?
C15A C14A H14A 120.3 . . ?
C15A C14A C13A 119.3(4) . . ?
C13A C14A H14A 120.3 . . ?
C12A C13A H13A 119.9 . . ?
C14A C13A C12A 120.2(4) . . ?
C14A C13A H13A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2B C2B C3B C8B -122.4(2) . . . . ?
O2B C2B C3B C4B 59.8(4) . . . . ?
O2B C2B C9B C11B -177.2(2) . . . . ?
O2B C2B C9B C10B -49.3(3) . . . . ?
O1B C1B C2B O2B -57.6(4) . . . . ?
O1B C1B C2B C3B -175.6(3) . . . . ?
O1B C1B C2B C9B 63.9(3) . . . . ?
O2A C2A C9A C11A 177.7(2) . . . . ?
O2A C2A C9A C10A 49.7(3) . . . . ?
O1A C1A C2A O2A 53.5(4) . . . . ?
O1A C1A C2A C3A 172.2(3) . . . . ?
O1A C1A C2A C9A -68.6(3) . . . . ?
N1A C1A C2A O2A -129.3(2) . . . . ?
N1A C1A C2A C3A -10.6(3) . . . . ?
N1A C1A C2A C9A 108.7(3) . . . . ?
N1A C8A C7A C6A -176.6(3) . . . . ?
N1B C1B C2B O2B 123.1(2) . . . . ?
N1B C1B C2B C3B 5.2(3) . . . . ?
N1B C1B C2B C9B -115.4(2) . . . . ?
N1B C8B C3B C4B -178.7(3) . . . . ?
N1B C8B C3B C2B 3.1(3) . . . . ?
C1A N1A C8A C3A -3.7(3) . . . . ?
C1A N1A C8A C7A 173.4(3) . . . . ?
C1A C2A C9A C11A -60.4(3) . . . . ?
C1A C2A C9A C10A 171.6(3) . . . . ?
C3A C2A C9A C11A 50.0(3) . . . . ?
C3A C2A C9A C10A -78.0(3) . . . . ?
C3A C8A C7A C6A 0.1(5) . . . . ?
C3A C4A C5A C6A -0.2(5) . . . . ?
C1B N1B C8B C7B -178.7(3) . . . . ?
C1B N1B C8B C3B 0.4(3) . . . . ?
C1B C2B C3B C8B -4.9(3) . . . . ?
C1B C2B C3B C4B 177.3(3) . . . . ?
C1B C2B C9B C11B 61.8(3) . . . . ?
C1B C2B C9B C10B -170.4(2) . . . . ?
C2A C3A C8A N1A -3.6(3) . . . . ?
C2A C3A C8A C7A 179.1(3) . . . . ?
C2A C3A C4A C5A -179.2(3) . . . . ?
C6B C7B C8B N1B 179.2(3) . . . . ?
C6B C7B C8B C3B 0.2(4) . . . . ?
C11A C16A C15A C14A -1.9(5) . . . . ?
C11A C12A C13A C14A -1.2(5) . . . . ?
C8A N1A C1A O1A -173.6(3) . . . . ?
C8A N1A C1A C2A 9.2(3) . . . . ?
C8A C3A C2A O2A 126.8(3) . . . . ?
C8A C3A C2A C1A 8.3(3) . . . . ?
C8A C3A C2A C9A -105.4(3) . . . . ?
C8A C3A C4A C5A 1.1(5) . . . . ?
C7B C6B C5B C4B -0.5(5) . . . . ?
C7B C8B C3B C4B 0.4(4) . . . . ?
C7B C8B C3B C2B -177.7(3) . . . . ?
C16A C11A C12A C13A -0.2(5) . . . . ?
C16A C11A C9A C2A -86.3(3) . . . . ?
C16A C11A C9A C10A 41.3(4) . . . . ?
C16A C15A C14A C13A 0.4(6) . . . . ?
C8B N1B C1B O1B 177.1(3) . . . . ?
C8B N1B C1B C2B -3.7(3) . . . . ?
C15A C14A C13A C12A 1.1(6) . . . . ?
C5B C6B C7B C8B -0.2(5) . . . . ?
C5B C4B C3B C8B -1.0(4) . . . . ?
C5B C4B C3B C2B 176.6(3) . . . . ?
C2B C9B C11B C12B 80.7(4) . . . . ?
C2B C9B C11B C16B -100.8(3) . . . . ?
C7A C6A C5A C4A -0.8(5) . . . . ?
C3B C4B C5B C6B 1.1(5) . . . . ?
C3B C2B C9B C11B -49.8(3) . . . . ?
C3B C2B C9B C10B 78.0(3) . . . . ?
C4A C3A C2A O2A -52.9(4) . . . . ?
C4A C3A C2A C1A -171.5(3) . . . . ?
C4A C3A C2A C9A 74.9(4) . . . . ?
C4A C3A C8A N1A 176.2(3) . . . . ?
C4A C3A C8A C7A -1.1(5) . . . . ?
C5A C6A C7A C8A 0.8(5) . . . . ?
C9B C2B C3B C8B 110.2(3) . . . . ?
C9B C2B C3B C4B -67.6(4) . . . . ?
C11B C12B C13B C14B -0.1(5) . . . . ?
C11B C16B C15B C14B -0.7(5) . . . . ?
C12A C11A C16A C15A 1.7(5) . . . . ?
C12A C11A C9A C2A 93.8(3) . . . . ?
C12A C11A C9A C10A -138.5(3) . . . . ?
C9A C11A C16A C15A -178.2(3) . . . . ?
C9A C11A C12A C13A 179.7(3) . . . . ?
C10B C9B C11B C12B -47.1(4) . . . . ?
C10B C9B C11B C16B 131.4(3) . . . . ?
C13B C12B C11B C16B -1.2(5) . . . . ?
C13B C12B C11B C9B 177.3(3) . . . . ?
C13B C14B C15B C16B -0.6(6) . . . . ?
C15B C14B C13B C12B 1.0(6) . . . . ?
C15B C16B C11B C12B 1.6(5) . . . . ?
C15B C16B C11B C9B -177.0(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.714
