# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_hn-cl
_database_code_depnum_ccdc_archive 'CCDC 2272209'
loop_
_audit_author_name
_audit_author_address
LJa
;Henan University
China
;
_audit_update_record             
;
2023-06-25 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-06-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Cl2 N O3'
_chemical_formula_sum            'C18 H13 Cl2 N O3'
_chemical_formula_weight         362.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   30.7988(15)
_cell_length_b                   4.6614(3)
_cell_length_c                   22.7529(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.524(5)
_cell_angle_gamma                90
_cell_volume                     3256.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4265
_cell_measurement_temperature    150.00(16)
_cell_measurement_theta_max      29.0220
_cell_measurement_theta_min      2.3260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6399
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  85.00   1.00   10.00    --   11.90  38.00   0.00   80
  2  ω    -16.00  85.00   1.00   10.00    --   11.90  57.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0226128000
_diffrn_orient_matrix_UB_12      0.0273018000
_diffrn_orient_matrix_UB_13      0.0007346000
_diffrn_orient_matrix_UB_21      -0.0022881000
_diffrn_orient_matrix_UB_22      0.0024895000
_diffrn_orient_matrix_UB_23      -0.0312695000
_diffrn_orient_matrix_UB_31      -0.0041953000
_diffrn_orient_matrix_UB_32      -0.1495395000
_diffrn_orient_matrix_UB_33      -0.0003867000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2421
_reflns_number_total             2875
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.9455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0970
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
;
_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 0.46980(2) 0.67030(13) 0.60687(3) 0.03801(19) Uani 1 1 d . . . . .
Cl2 Cl 0.43131(2) -0.04428(10) 0.42564(2) 0.02952(17) Uani 1 1 d . . . . .
O1 O 0.30101(4) 0.8081(3) 0.54012(6) 0.0273(4) Uani 1 1 d . . . . .
O2 O 0.26211(5) 0.5733(3) 0.32000(7) 0.0295(4) Uani 1 1 d . . . . .
O3 O 0.20144(4) 0.3085(3) 0.31963(6) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.28569(5) 0.4963(3) 0.46476(7) 0.0219(4) Uani 1 1 d . . . . .
H1 H 0.258370 0.553348 0.462694 0.026 Uiso 1 1 calc R U . . .
C1 C 0.31377(6) 0.6213(4) 0.50656(9) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.35862(6) 0.5156(4) 0.50923(9) 0.0206(4) Uani 1 1 d . . . . .
C3 C 0.38880(6) 0.6267(4) 0.55246(9) 0.0244(5) Uani 1 1 d . . . . .
H3 H 0.380260 0.767716 0.579409 0.029 Uiso 1 1 calc R U . . .
C4 C 0.43086(7) 0.5290(4) 0.55536(9) 0.0258(5) Uani 1 1 d . . . . .
C5 C 0.44413(7) 0.3204(4) 0.51651(9) 0.0256(5) Uani 1 1 d . . . . .
H5 H 0.473392 0.254207 0.519283 0.031 Uiso 1 1 calc R U . . .
C6 C 0.41430(7) 0.2128(4) 0.47434(9) 0.0235(5) Uani 1 1 d . . . . .
C7 C 0.37043(6) 0.3052(4) 0.46884(9) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.33818(7) 0.1939(4) 0.42623(9) 0.0233(5) Uani 1 1 d . . . . .
H8 H 0.345946 0.054195 0.398525 0.028 Uiso 1 1 calc R U . . .
C9 C 0.29662(7) 0.2877(4) 0.42544(9) 0.0221(5) Uani 1 1 d . . . . .
C10 C 0.25954(7) 0.1713(4) 0.38582(10) 0.0260(5) Uani 1 1 d . . . . .
H10A H 0.235612 0.116891 0.410210 0.031 Uiso 1 1 calc R U . . .
H10B H 0.269389 -0.004966 0.366565 0.031 Uiso 1 1 calc R U . . .
C11 C 0.24205(6) 0.3776(4) 0.33886(9) 0.0209(5) Uani 1 1 d . . . . .
C12 C 0.18152(7) 0.4891(5) 0.27253(10) 0.0311(5) Uani 1 1 d . . . . .
H12A H 0.199689 0.490667 0.238528 0.037 Uiso 1 1 calc R U . . .
H12B H 0.178581 0.688541 0.286647 0.037 Uiso 1 1 calc R U . . .
C13 C 0.13763(7) 0.3646(4) 0.25489(9) 0.0260(5) Uani 1 1 d . . . . .
C14 C 0.13261(7) 0.1616(4) 0.21056(10) 0.0298(5) Uani 1 1 d . . . . .
H14 H 0.157092 0.103480 0.190600 0.036 Uiso 1 1 calc R U . . .
C15 C 0.09206(7) 0.0424(5) 0.19504(10) 0.0349(6) Uani 1 1 d . . . . .
H15 H 0.088809 -0.097313 0.164611 0.042 Uiso 1 1 calc R U . . .
C16 C 0.05649(7) 0.1273(5) 0.22390(10) 0.0355(6) Uani 1 1 d . . . . .
H16 H 0.028669 0.046190 0.213292 0.043 Uiso 1 1 calc R U . . .
C17 C 0.06121(8) 0.3286(5) 0.26793(11) 0.0408(6) Uani 1 1 d . . . . .
H17 H 0.036709 0.385875 0.287955 0.049 Uiso 1 1 calc R U . . .
C18 C 0.10142(8) 0.4476(5) 0.28308(11) 0.0376(6) Uani 1 1 d . . . . .
H18 H 0.104379 0.588653 0.313270 0.045 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 C4 1.739(2) . ?
Cl2 C6 1.741(2) . ?
O1 C1 1.242(2) . ?
O2 C11 1.200(2) . ?
O3 C11 1.332(2) . ?
O3 C12 1.459(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.365(3) . ?
N1 C9 1.381(3) . ?
C1 C2 1.463(3) . ?
C2 C3 1.398(3) . ?
C2 C7 1.411(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(3) . ?
C4 C5 1.396(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(3) . ?
C6 C7 1.414(3) . ?
C7 C8 1.430(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.351(3) . ?
C9 C10 1.499(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.496(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(3) . ?
C18 H18 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
C11 O3 C12 115.55(15) . . ?
C1 N1 H1 117.3 . . ?
C1 N1 C9 125.35(17) . . ?
C9 N1 H1 117.3 . . ?
O1 C1 N1 120.91(18) . . ?
O1 C1 C2 123.64(18) . . ?
N1 C1 C2 115.44(17) . . ?
C3 C2 C1 118.51(18) . . ?
C3 C2 C7 121.61(18) . . ?
C7 C2 C1 119.87(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Cl1 120.38(17) . . ?
C3 C4 C5 121.59(19) . . ?
C5 C4 Cl1 118.01(16) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.98(19) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 Cl2 118.62(16) . . ?
C5 C6 C7 122.25(19) . . ?
C7 C6 Cl2 119.13(15) . . ?
C2 C7 C6 116.60(18) . . ?
C2 C7 C8 119.51(18) . . ?
C6 C7 C8 123.88(19) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.89(19) . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C10 115.55(17) . . ?
C8 C9 N1 119.89(18) . . ?
C8 C9 C10 124.51(19) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C9 C10 C11 114.12(16) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O2 C11 O3 124.27(18) . . ?
O2 C11 C10 125.02(18) . . ?
O3 C11 C10 110.68(16) . . ?
O3 C12 H12A 110.3 . . ?
O3 C12 H12B 110.3 . . ?
O3 C12 C13 106.96(16) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 C18 118.8(2) . . ?
C18 C13 C12 120.7(2) . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 119.6 . . ?

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
Cl1 C4 C5 C6 -177.94(15) . . . . ?
Cl2 C6 C7 C2 -179.49(14) . . . . ?
Cl2 C6 C7 C8 1.9(3) . . . . ?
O1 C1 C2 C3 1.1(3) . . . . ?
O1 C1 C2 C7 -179.20(18) . . . . ?
O3 C12 C13 C14 -90.6(2) . . . . ?
O3 C12 C13 C18 88.6(2) . . . . ?
N1 C1 C2 C3 -177.71(17) . . . . ?
N1 C1 C2 C7 2.0(3) . . . . ?
N1 C9 C10 C11 71.7(2) . . . . ?
C1 N1 C9 C8 -0.6(3) . . . . ?
C1 N1 C9 C10 176.71(17) . . . . ?
C1 C2 C3 C4 179.95(18) . . . . ?
C1 C2 C7 C6 -179.71(17) . . . . ?
C1 C2 C7 C8 -1.0(3) . . . . ?
C2 C3 C4 Cl1 177.85(15) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C7 C8 C9 -0.9(3) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C3 C2 C7 C8 178.69(18) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 Cl2 179.32(15) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C5 C6 C7 C8 -178.68(18) . . . . ?
C6 C7 C8 C9 177.72(18) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C7 C8 C9 N1 1.7(3) . . . . ?
C7 C8 C9 C10 -175.35(17) . . . . ?
C8 C9 C10 C11 -111.1(2) . . . . ?
C9 N1 C1 O1 179.92(18) . . . . ?
C9 N1 C1 C2 -1.2(3) . . . . ?
C9 C10 C11 O2 23.8(3) . . . . ?
C9 C10 C11 O3 -157.99(17) . . . . ?
C11 O3 C12 C13 176.35(17) . . . . ?
C12 O3 C11 O2 0.0(3) . . . . ?
C12 O3 C11 C10 -178.17(17) . . . . ?
C12 C13 C14 C15 178.75(19) . . . . ?
C12 C13 C18 C17 -178.4(2) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C13 C18 C17 0.8(3) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C18 C13 C14 C15 -0.5(3) . . . . ?

_olex2_date_sample_data_collection 2023-06-07
_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_br0525
_database_code_depnum_ccdc_archive 'CCDC 2272211'
loop_
_audit_author_name
_audit_author_address
LJb
;Henan University
China
;
_audit_update_record             
;
2023-06-25 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2023-05-31
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 Br N2 O3'
_chemical_formula_sum            'C20 H15 Br N2 O3'
_chemical_formula_weight         411.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.3629(4)
_cell_length_b                   17.7232(15)
_cell_length_c                   18.1847(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.638(8)
_cell_angle_gamma                90
_cell_volume                     1722.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2297
_cell_measurement_temperature    150.00(18)
_cell_measurement_theta_max      73.6300
_cell_measurement_theta_min      3.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_av_unetI/netI     0.1316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6971
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.912
_diffrn_reflns_theta_min         3.488
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00   3.00   1.00    1.50    --  -40.92  57.00 120.00   63
  2  ω      7.00  32.00   1.00    1.50    --  -40.92  57.00 120.00   25
  3  ω     70.00  97.00   1.00    1.50    --   40.92-125.00 -90.00   27
  4  ω     88.00 113.00   1.00    2.00    --  107.58-104.00 -93.00   25
  5  ω     72.00 137.00   1.00    2.00    --  107.58 -77.00-180.00   65
  6  ω     41.00  71.00   1.00    2.00    --  107.58 -94.00-180.00   30
  7  ω     32.00 135.00   1.00    2.00    --  107.58 -30.00 -90.00  103
  8  ω    126.00 178.00   1.00    2.00    --  107.58  61.00-120.00   52
  9  ω    102.00 166.00   1.00    2.00    --  107.58  77.00 -90.00   64
 10  ω     35.00  61.00   1.00    2.00    --  107.58-104.00 -93.00   26
 11  ω     36.00 122.00   1.00    2.00    --  107.58-125.00 120.00   86
 12  ω   -115.00 -19.00   1.00    1.50    --  -40.92 -37.00 -30.00   96
 13  ω   -106.00 -76.00   1.00    1.50    --  -41.23 -37.00 120.00   30
 14  ω   -109.00 -64.00   1.00    1.50    --  -41.23 -57.00-120.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0501926000
_diffrn_orient_matrix_UB_12      -0.0603894000
_diffrn_orient_matrix_UB_13      -0.0603509000
_diffrn_orient_matrix_UB_21      0.0869910000
_diffrn_orient_matrix_UB_22      -0.0619791000
_diffrn_orient_matrix_UB_23      0.0556600000
_diffrn_orient_matrix_UB_31      -0.2701064000
_diffrn_orient_matrix_UB_32      -0.0086507000
_diffrn_orient_matrix_UB_33      0.0218635000
_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                2494
_reflns_number_total             3388
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.675
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     363
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0913
_refine_ls_restrained_S_all      1.043
_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)+(0.1795P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2469
_refine_ls_wR_factor_ref         0.2834
_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. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(Br1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N1)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O2)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18)
\\sim Ueq, : with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Rigid body (RIGU) restrains
 Br1, O1, O2, O3, N1, N2, H2, C1, C2, H2A, C3, H3, C4, C5, H5, C6, C7, H7, C8,
 C9, C10, H10, C11, C12, H12A, H12B, C13, C14, H14A, H14B, C15, C16, H16, C17,
 H17, C18, H18, C19, H19, C20, H20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C7(H7), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_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
Br1 Br 1.04178(14) 0.31235(4) 0.68268(4) 0.0382(3) Uani 1 1 d . U . . .
O1 O 0.2847(7) 0.4660(2) 0.5463(2) 0.0203(8) Uani 1 1 d . U . . .
O2 O 0.7279(7) 0.7896(2) 0.5679(2) 0.0267(9) Uani 1 1 d . U . . .
O3 O 0.5256(7) 0.8882(2) 0.6126(2) 0.0208(8) Uani 1 1 d . U . . .
N1 N 0.4971(8) 0.5588(3) 0.6123(2) 0.0157(8) Uani 1 1 d . U . . .
N2 N 0.1402(9) 0.5872(3) 0.5378(2) 0.0195(8) Uani 1 1 d . U . . .
H2 H 0.021959 0.574014 0.505549 0.023 Uiso 1 1 calc R U . . .
C1 C 0.8436(10) 0.5682(3) 0.6908(3) 0.0187(9) Uani 1 1 d . U . . .
C2 C 1.0580(11) 0.5408(3) 0.7313(3) 0.0216(10) Uani 1 1 d . U . . .
H2A H 1.161931 0.573139 0.759938 0.026 Uiso 1 1 calc R U . . .
C3 C 1.1122(10) 0.4644(3) 0.7278(3) 0.0215(10) Uani 1 1 d . U . . .
H3 H 1.256140 0.445522 0.753320 0.026 Uiso 1 1 calc R U . . .
C4 C 0.9520(11) 0.4156(3) 0.6862(3) 0.0231(10) Uani 1 1 d . U . . .
C5 C 0.7407(10) 0.4401(3) 0.6449(3) 0.0189(9) Uani 1 1 d . U . . .
H5 H 0.637600 0.406971 0.616744 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6900(10) 0.5171(3) 0.6475(3) 0.0177(9) Uani 1 1 d . U . . .
C7 C 0.7358(10) 0.6420(3) 0.6809(3) 0.0205(9) Uani 1 1 d . U . . .
H7 H 0.797856 0.686238 0.702921 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5284(10) 0.6357(3) 0.6340(3) 0.0182(9) Uani 1 1 d . U . . .
C9 C 0.3426(11) 0.6877(3) 0.6053(3) 0.0198(9) Uani 1 1 d . U . . .
C10 C 0.1533(10) 0.6619(3) 0.5591(3) 0.0202(9) Uani 1 1 d . U . . .
H10 H 0.028513 0.695065 0.541214 0.024 Uiso 1 1 calc R U . . .
C11 C 0.3048(9) 0.5325(3) 0.5648(3) 0.0151(8) Uani 1 1 d . U . . .
C12 C 0.3475(10) 0.7689(3) 0.6306(3) 0.0204(9) Uani 1 1 d . U . . .
H12A H 0.368454 0.770209 0.684066 0.025 Uiso 1 1 calc R U . . .
H12B H 0.188017 0.792226 0.615317 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5562(10) 0.8148(3) 0.6000(3) 0.0191(9) Uani 1 1 d . U . . .
C14 C 0.7074(10) 0.9371(3) 0.5826(3) 0.0206(10) Uani 1 1 d . U . . .
H14A H 0.717509 0.925756 0.530704 0.025 Uiso 1 1 calc R U . . .
H14B H 0.870844 0.928324 0.608016 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6347(10) 1.0178(3) 0.5912(3) 0.0192(9) Uani 1 1 d . U . . .
C16 C 0.4326(10) 1.0414(3) 0.6281(3) 0.0218(10) Uani 1 1 d . U . . .
H16 H 0.329947 1.006100 0.648367 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3830(11) 1.1184(3) 0.6347(3) 0.0238(10) Uani 1 1 d . U . . .
H17 H 0.247280 1.133655 0.659776 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5303(12) 1.1719(4) 0.6049(3) 0.0262(11) Uani 1 1 d . U . . .
H18 H 0.494419 1.223017 0.609092 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7325(11) 1.1482(4) 0.5687(3) 0.0275(11) Uani 1 1 d . U . . .
H19 H 0.834748 1.184024 0.548871 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7872(11) 1.0719(3) 0.5612(3) 0.0236(10) Uani 1 1 d . U . . .
H20 H 0.924114 1.057003 0.536466 0.028 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
Br1 C4 1.895(6) . ?
O1 C11 1.228(6) . ?
O2 C13 1.214(7) . ?
O3 C13 1.333(7) . ?
O3 C14 1.444(6) . ?
N1 C6 1.386(7) . ?
N1 C8 1.425(7) . ?
N1 C11 1.372(6) . ?
N2 H2 0.8600 . ?
N2 C10 1.380(7) . ?
N2 C11 1.374(7) . ?
C1 C2 1.401(7) . ?
C1 C6 1.419(7) . ?
C1 C7 1.435(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.387(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(8) . ?
C4 C5 1.378(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.350(7) . ?
C8 C9 1.425(7) . ?
C9 C10 1.344(8) . ?
C9 C12 1.512(7) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.525(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.495(8) . ?
C15 C16 1.384(7) . ?
C15 C20 1.399(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(8) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O3 C14 115.1(4) . . ?
C6 N1 C8 108.4(4) . . ?
C11 N1 C6 127.2(5) . . ?
C11 N1 C8 124.4(5) . . ?
C10 N2 H2 118.0 . . ?
C11 N2 H2 118.0 . . ?
C11 N2 C10 124.0(5) . . ?
C2 C1 C6 119.0(5) . . ?
C2 C1 C7 133.4(5) . . ?
C6 C1 C7 107.6(5) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 C1 118.8(5) . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 Br1 117.9(4) . . ?
C5 C4 Br1 119.0(4) . . ?
C5 C4 C3 123.0(5) . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.3(5) . . ?
C6 C5 H5 121.9 . . ?
N1 C6 C1 107.1(5) . . ?
N1 C6 C5 130.3(5) . . ?
C5 C6 C1 122.6(5) . . ?
C1 C7 H7 126.1 . . ?
C8 C7 C1 107.9(5) . . ?
C8 C7 H7 126.1 . . ?
C7 C8 N1 109.0(5) . . ?
C7 C8 C9 134.0(5) . . ?
C9 C8 N1 116.9(5) . . ?
C8 C9 C12 120.6(5) . . ?
C10 C9 C8 118.7(5) . . ?
C10 C9 C12 120.5(5) . . ?
N2 C10 H10 119.3 . . ?
C9 C10 N2 121.4(5) . . ?
C9 C10 H10 119.3 . . ?
O1 C11 N1 122.9(5) . . ?
O1 C11 N2 122.6(5) . . ?
N1 C11 N2 114.5(5) . . ?
C9 C12 H12A 109.0 . . ?
C9 C12 H12B 109.0 . . ?
C9 C12 C13 113.1(4) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
O2 C13 O3 123.4(5) . . ?
O2 C13 C12 125.9(5) . . ?
O3 C13 C12 110.7(5) . . ?
O3 C14 H14A 109.6 . . ?
O3 C14 H14B 109.6 . . ?
O3 C14 C15 110.2(4) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C16 C15 C14 124.2(5) . . ?
C16 C15 C20 119.1(5) . . ?
C20 C15 C14 116.7(5) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.5(6) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.5(6) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.5(5) . . ?
C19 C20 H20 120.2 . . ?

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
Br1 C4 C5 C6 -177.6(4) . . . . ?
O3 C14 C15 C16 4.7(8) . . . . ?
O3 C14 C15 C20 -176.9(5) . . . . ?
N1 C8 C9 C10 -1.0(7) . . . . ?
N1 C8 C9 C12 174.5(4) . . . . ?
C1 C2 C3 C4 -1.7(8) . . . . ?
C1 C7 C8 N1 -0.2(6) . . . . ?
C1 C7 C8 C9 178.0(6) . . . . ?
C2 C1 C6 N1 -178.6(5) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
C2 C1 C7 C8 178.7(6) . . . . ?
C2 C3 C4 Br1 178.9(4) . . . . ?
C2 C3 C4 C5 2.4(9) . . . . ?
C3 C4 C5 C6 -1.2(8) . . . . ?
C4 C5 C6 N1 179.2(5) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C6 N1 C8 C7 0.6(6) . . . . ?
C6 N1 C8 C9 -178.0(5) . . . . ?
C6 N1 C11 O1 -1.6(8) . . . . ?
C6 N1 C11 N2 -179.7(5) . . . . ?
C6 C1 C2 C3 -0.1(8) . . . . ?
C6 C1 C7 C8 -0.2(6) . . . . ?
C7 C1 C2 C3 -178.9(6) . . . . ?
C7 C1 C6 N1 0.5(6) . . . . ?
C7 C1 C6 C5 -179.6(5) . . . . ?
C7 C8 C9 C10 -179.1(6) . . . . ?
C7 C8 C9 C12 -3.6(9) . . . . ?
C8 N1 C6 C1 -0.6(5) . . . . ?
C8 N1 C6 C5 179.4(5) . . . . ?
C8 N1 C11 O1 179.0(5) . . . . ?
C8 N1 C11 N2 0.9(7) . . . . ?
C8 C9 C10 N2 -1.9(8) . . . . ?
C8 C9 C12 C13 72.8(6) . . . . ?
C9 C12 C13 O2 -10.8(8) . . . . ?
C9 C12 C13 O3 168.7(4) . . . . ?
C10 N2 C11 O1 178.0(5) . . . . ?
C10 N2 C11 N1 -4.0(7) . . . . ?
C10 C9 C12 C13 -111.8(6) . . . . ?
C11 N1 C6 C1 179.9(4) . . . . ?
C11 N1 C6 C5 -0.1(9) . . . . ?
C11 N1 C8 C7 -179.9(5) . . . . ?
C11 N1 C8 C9 1.5(7) . . . . ?
C11 N2 C10 C9 4.6(8) . . . . ?
C12 C9 C10 N2 -177.4(5) . . . . ?
C13 O3 C14 C15 172.4(4) . . . . ?
C14 O3 C13 O2 2.4(8) . . . . ?
C14 O3 C13 C12 -177.2(4) . . . . ?
C14 C15 C16 C17 178.5(5) . . . . ?
C14 C15 C20 C19 -178.7(5) . . . . ?
C15 C16 C17 C18 0.4(9) . . . . ?
C16 C15 C20 C19 -0.2(8) . . . . ?
C16 C17 C18 C19 -0.8(9) . . . . ?
C17 C18 C19 C20 0.8(10) . . . . ?
C18 C19 C20 C15 -0.2(10) . . . . ?
C20 C15 C16 C17 0.2(8) . . . . ?

_olex2_date_sample_data_collection 2023-05-25
_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 3.385
_oxdiff_exptl_absorpt_empirical_full_min 0.343
