# 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_al332
_database_code_depnum_ccdc_archive 'CCDC 2337550'
loop_
_audit_author_name
_audit_author_address
'Svetlana Aksenova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-03-04 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_audit_creation_date             2024-03-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl N O'
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69
_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           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                   7.37990(10)
_cell_length_b                   13.7636(3)
_cell_length_c                   11.7474(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.6480(10)
_cell_angle_gamma                90
_cell_volume                     1192.74(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0384 after correction.
The Ratio of minimum to maximum transmission is 0.9129.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         2.280
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2982
_reflns_number_total             3168
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.038
_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)+(0.0390P)²+0.5323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0815
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C6(H6), C14(H14), C11(H11), C4(H4), C12(H12), C3(H3), C5(H5)
2.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_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 0.43473(4) 0.96796(2) 0.64314(2) 0.02408(9) Uani 1 1 d . . . . .
O1 O 0.07760(11) 0.43458(6) 0.78266(6) 0.02072(17) Uani 1 1 d . . . . .
N1 N 0.12880(12) 0.51609(7) 0.71732(8) 0.01902(18) Uani 1 1 d . . . . .
C10 C 0.28964(13) 0.65513(7) 0.56612(8) 0.01407(18) Uani 1 1 d . . . . .
C7 C 0.19898(13) 0.48322(7) 0.62349(8) 0.01490(18) Uani 1 1 d . . . . .
C2 C 0.12167(13) 0.35332(8) 0.72376(8) 0.01658(19) Uani 1 1 d . . . . .
C15 C 0.38051(13) 0.68036(7) 0.66804(8) 0.01597(19) Uani 1 1 d . . . . .
H15 H 0.4123 0.6311 0.7216 0.019 Uiso 1 1 calc R U . . .
C8 C 0.25268(13) 0.55243(7) 0.53476(8) 0.01483(18) Uani 1 1 d . . . . .
C1 C 0.20121(13) 0.37841(7) 0.62183(8) 0.01433(18) Uani 1 1 d . . . . .
C6 C 0.26068(13) 0.30447(7) 0.54938(8) 0.01584(19) Uani 1 1 d . . . . .
H6 H 0.3185 0.3194 0.4803 0.019 Uiso 1 1 calc R U . . .
C14 C 0.42490(13) 0.77633(8) 0.69211(8) 0.01685(19) Uani 1 1 d . . . . .
H14 H 0.4882 0.7927 0.7610 0.020 Uiso 1 1 calc R U . . .
C11 C 0.23928(13) 0.72965(7) 0.49039(8) 0.01634(19) Uani 1 1 d . . . . .
H11 H 0.1748 0.7138 0.4217 0.020 Uiso 1 1 calc R U . . .
C13 C 0.37559(14) 0.84806(7) 0.61415(8) 0.01695(19) Uani 1 1 d . . . . .
C4 C 0.14691(14) 0.18650(8) 0.68397(9) 0.0199(2) Uani 1 1 d . . . . .
H4 H 0.1278 0.1203 0.7030 0.024 Uiso 1 1 calc R U . . .
C12 C 0.28151(14) 0.82606(7) 0.51339(9) 0.0178(2) Uani 1 1 d . . . . .
H12 H 0.2468 0.8759 0.4613 0.021 Uiso 1 1 calc R U . . .
C3 C 0.09003(14) 0.25815(8) 0.75760(9) 0.0196(2) Uani 1 1 d . . . . .
H3 H 0.0330 0.2432 0.8269 0.024 Uiso 1 1 calc R U . . .
C5 C 0.23227(14) 0.20921(8) 0.58185(9) 0.0189(2) Uani 1 1 d . . . . .
H5 H 0.2713 0.1580 0.5341 0.023 Uiso 1 1 calc R U . . .
C9 C 0.26262(15) 0.52241(8) 0.42677(9) 0.0207(2) Uani 1 1 d . . . . .
H9A H 0.2352 0.4569 0.4077 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2971 0.5666 0.3692 0.025 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 C13 1.7383(10) . ?
O1 N1 1.4168(11) . ?
O1 C2 1.3596(13) . ?
N1 C7 1.3118(13) . ?
C10 C15 1.3992(13) . ?
C10 C8 1.4841(13) . ?
C10 C11 1.4008(13) . ?
C7 C8 1.4747(14) . ?
C7 C1 1.4428(13) . ?
C2 C1 1.3921(13) . ?
C2 C3 1.3905(14) . ?
C15 H15 0.9500 . ?
C15 C14 1.3880(14) . ?
C8 C9 1.3382(14) . ?
C1 C6 1.4050(14) . ?
C6 H6 0.9500 . ?
C6 C5 1.3832(14) . ?
C14 H14 0.9500 . ?
C14 C13 1.3881(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.3879(14) . ?
C13 C12 1.3883(14) . ?
C4 H4 0.9500 . ?
C4 C3 1.3848(16) . ?
C4 C5 1.4062(15) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C9 H9A 0.9500 . ?
C9 H9B 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
C2 O1 N1 107.72(7) . . ?
C7 N1 O1 107.46(8) . . ?
C15 C10 C8 121.93(9) . . ?
C15 C10 C11 118.27(9) . . ?
C11 C10 C8 119.75(9) . . ?
N1 C7 C8 119.45(9) . . ?
N1 C7 C1 111.17(9) . . ?
C1 C7 C8 129.26(9) . . ?
O1 C2 C1 110.28(9) . . ?
O1 C2 C3 125.79(9) . . ?
C3 C2 C1 123.91(10) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.00(9) . . ?
C14 C15 H15 119.5 . . ?
C7 C8 C10 119.41(9) . . ?
C9 C8 C10 120.98(9) . . ?
C9 C8 C7 119.59(9) . . ?
C2 C1 C7 103.36(8) . . ?
C2 C1 C6 119.22(9) . . ?
C6 C1 C7 137.41(9) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.84(9) . . ?
C5 C6 H6 121.1 . . ?
C15 C14 H14 120.4 . . ?
C13 C14 C15 119.11(9) . . ?
C13 C14 H14 120.4 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.49(9) . . ?
C12 C11 H11 119.3 . . ?
C14 C13 Cl1 119.10(8) . . ?
C14 C13 C12 121.51(9) . . ?
C12 C13 Cl1 119.39(8) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.72(10) . . ?
C5 C4 H4 119.1 . . ?
C11 C12 C13 118.59(9) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C2 C3 H3 122.1 . . ?
C4 C3 C2 115.84(9) . . ?
C4 C3 H3 122.1 . . ?
C6 C5 C4 121.41(10) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?

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 C13 C12 C11 178.46(8) . . . . ?
O1 N1 C7 C8 175.61(8) . . . . ?
O1 N1 C7 C1 -0.93(11) . . . . ?
O1 C2 C1 C7 -0.81(11) . . . . ?
O1 C2 C1 C6 178.55(8) . . . . ?
O1 C2 C3 C4 -179.87(9) . . . . ?
N1 O1 C2 C1 0.30(11) . . . . ?
N1 O1 C2 C3 -178.53(10) . . . . ?
N1 C7 C8 C10 21.78(14) . . . . ?
N1 C7 C8 C9 -156.43(10) . . . . ?
N1 C7 C1 C2 1.09(11) . . . . ?
N1 C7 C1 C6 -178.08(11) . . . . ?
C10 C15 C14 C13 0.92(15) . . . . ?
C10 C11 C12 C13 -0.10(15) . . . . ?
C7 C1 C6 C5 -179.13(11) . . . . ?
C2 O1 N1 C7 0.40(11) . . . . ?
C2 C1 C6 C5 1.80(14) . . . . ?
C15 C10 C8 C7 39.27(13) . . . . ?
C15 C10 C8 C9 -142.54(11) . . . . ?
C15 C10 C11 C12 1.60(15) . . . . ?
C15 C14 C13 Cl1 -178.86(8) . . . . ?
C15 C14 C13 C12 0.65(15) . . . . ?
C8 C10 C15 C14 175.46(9) . . . . ?
C8 C10 C11 C12 -175.92(9) . . . . ?
C8 C7 C1 C2 -175.03(10) . . . . ?
C8 C7 C1 C6 5.81(19) . . . . ?
C1 C7 C8 C10 -162.38(9) . . . . ?
C1 C7 C8 C9 19.41(16) . . . . ?
C1 C2 C3 C4 1.46(15) . . . . ?
C1 C6 C5 C4 -0.06(15) . . . . ?
C14 C13 C12 C11 -1.05(15) . . . . ?
C11 C10 C15 C14 -2.01(15) . . . . ?
C11 C10 C8 C7 -143.29(9) . . . . ?
C11 C10 C8 C9 34.89(14) . . . . ?
C3 C2 C1 C7 178.05(9) . . . . ?
C3 C2 C1 C6 -2.60(15) . . . . ?
C3 C4 C5 C6 -1.06(16) . . . . ?
C5 C4 C3 C2 0.38(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AL538
_database_code_depnum_ccdc_archive 'CCDC 2346577'
loop_
_audit_author_name
_audit_author_address
'Vladislav Lesnikov'
;ZIOC RAS
Russia
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-04-10 downloaded from the CCDC.
;
_audit_creation_date             2024-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 Br N O3'
_chemical_formula_sum            'C19 H18 Br N O3'
_chemical_formula_weight         388.25
_chemical_melting_point          394-396
_chemical_oxdiff_formula         C19H18BrNO3
_chemical_oxdiff_usercomment     AL538
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                   8.15719(7)
_cell_length_b                   16.71710(15)
_cell_length_c                   12.13404(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.3390(7)
_cell_angle_gamma                90
_cell_volume                     1653.27(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15936
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.8150
_cell_measurement_theta_min      4.4770
_shelx_estimated_absorpt_T_max   0.531
_shelx_estimated_absorpt_T_min   0.253
_exptl_absorpt_coefficient_mu    3.534
_exptl_absorpt_correction_T_max  0.664
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.117a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 -1 0.1349
0 2 1 0.1980
0 1 -2 0.2029
-2 -1 -1 0.0664
1 1 0 0.0798
1 0 0 0.0552
1 -1 1 0.1848
0 1 -1 0.1843
0 2 -1 0.1847
-1 1 1 0.2557
0 -2 1 0.2301
1 0 -2 0.1717
0 1 0 0.1481
-2 0 -1 0.0675
1 -1 0 0.0467
1 1 1 0.1884
2 2 1 0.1310

_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.205
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -2.0000 -1.0000 0.1294 -0.1827 0.0003
-0.0000 2.0000 1.0000 -0.1294 0.1827 -0.0003
-0.0000 1.0000 -2.0000 0.1282 0.0073 0.2378
-2.0000 -1.0000 -1.0000 0.3929 0.0862 -0.0981
1.0000 1.0000 -0.0000 -0.1709 -0.0226 0.1204
1.0000 0.0000 0.0000 -0.1448 -0.0972 0.0729
1.0000 -1.0000 1.0000 -0.1959 -0.1381 -0.0697
-0.0000 1.0000 -1.0000 0.0511 0.0410 0.1426
-0.0000 2.0000 -1.0000 0.0250 0.1155 0.1900
-1.0000 1.0000 1.0000 0.0415 0.2054 -0.1207
0.0000 -2.0000 1.0000 -0.0250 -0.1155 -0.1900
1.0000 0.0000 -2.0000 0.0095 -0.1644 0.2633
-0.0000 1.0000 -0.0000 -0.0261 0.0746 0.0474
-2.0000 0.0000 -1.0000 0.3668 0.1608 -0.0507
1.0000 -1.0000 0.0000 -0.1187 -0.1717 0.0255
1.0000 1.0000 1.0000 -0.2481 0.0110 0.0252
2.0000 2.0000 1.0000 -0.4190 -0.0116 0.1456

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19247
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.103
_diffrn_reflns_theta_min         4.505
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -23.00   0.50    0.20    --  -93.75  45.00-150.00   50
  2  ω    -26.00  31.00   0.50    0.05    --  -44.88  19.00 -30.00  114
  3  ω    -72.00  29.00   0.50    0.05    --  -44.88  80.00  -9.00  202
  4  ω   -121.00 -20.00   0.50    0.20    --  -93.75  80.00  -9.00  202
  5  ω    -40.00  29.00   0.50    0.05    --  -44.88  38.00  90.00  138
  6  ω     60.00  89.00   0.50    0.05    --   44.88-125.00  60.00   58
  7  ω     51.00  92.00   0.50    0.20    --  115.25 -95.00   0.00   82
  8  ω     47.00  73.00   0.50    0.20    --  115.25-125.00   0.00   52
  9  ω     53.00 109.00   0.50    0.20    --  115.25-125.00 -60.00  112
 10  ω     46.00 105.00   0.50    0.20    --  115.25-125.00-150.00  118
 11  ω     50.00  76.00   0.50    0.20    --  115.25 -87.00 -45.65   52
 12  ω     65.00  91.00   0.50    0.20    --  115.25 -95.00 -60.00   52
 13  ω     73.00  99.00   0.50    0.20    --  115.25 -95.00 -30.00   52
 14  ω     87.00 113.00   0.50    0.20    --  115.25 -87.00 -45.65   52
 15  ω     65.00 102.00   0.50    0.20    --  115.25 -95.00  90.00   74
 16  ω     86.00 115.00   0.50    0.20    --  115.25 -85.00  81.16   58
 17  ω    -21.00  72.00   0.50    0.05    --   44.88 -80.00-132.00  186
 18  ω     43.00 138.00   0.50    0.20    --  115.25 -80.00-132.00  190
 19  ω    113.00 139.00   0.50    0.20    --  115.25 -80.00-132.00   52
 20  ω     44.00  71.00   0.50    0.20    --  115.25 -61.00-180.00   54
 21  ω     43.00  68.00   0.50    0.20    --  115.25 -61.00 -90.00   50
 22  ω     46.00  71.00   0.50    0.20    --  115.25 -61.00   0.00   50
 23  ω     46.00  72.00   0.50    0.20    --  115.25 -77.00  60.00   52
 24  ω     49.00 104.00   0.50    0.20    --  115.25 -77.00  90.00  110
 25  ω     48.00 104.00   0.50    0.20    --  115.25 -77.00 150.00  112
 26  ω     43.00  68.00   0.50    0.20    --  115.25 -61.00  60.00   50
 27  ω    -24.00   2.00   0.50    0.05    --   44.88 -19.00-180.00   52
 28  ω     90.00 139.00   0.50    0.20    --  115.25  15.00-120.00   98
 29  ω    146.00 172.00   0.50    0.20    --  115.25  77.00 -60.00   52
 30  ω    101.00 129.00   0.50    0.20    --  115.25  80.00  -9.00   56
 31  ω     98.00 124.00   0.50    0.20    --  115.25  61.00 -60.00   52
 32  ω     97.00 123.00   0.50    0.20    --  115.25  77.00 -60.00   52
 33  ω    102.00 127.00   0.50    0.20    --  115.25  61.00-120.00   50
 34  ω    146.00 177.00   0.50    0.20    --  115.25  61.00-120.00   62
 35  ω    133.00 169.00   0.50    0.20    --  115.25  30.00-180.00   72
 36  ω     98.00 171.00   0.50    0.20    --  115.25  45.00 -60.00  146
 37  ω    101.00 157.00   0.50    0.20    --  115.25  30.00 -60.00  112
 38  ω    107.00 156.00   0.50    0.20    --  115.25  45.00 -30.00   98
 39  ω     93.00 150.00   0.50    0.20    --  115.25  15.00  90.00  114
 40  ω    101.00 176.00   0.50    0.20    --  115.25  61.00 120.00  150
 41  ω    140.00 173.00   0.50    0.20    --  115.25 125.00  60.00   66
 42  ω     96.00 123.00   0.50    0.20    --  115.25 125.00 -60.00   54
 43  ω    144.00 170.00   0.50    0.20    --  115.25 125.00 -60.00   52
 44  ω   -167.00 -79.00   0.50    0.20    --  -93.75 -80.00-132.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1448128000
_diffrn_orient_matrix_UB_12      -0.0261042000
_diffrn_orient_matrix_UB_13      -0.0771731000
_diffrn_orient_matrix_UB_21      -0.0971855000
_diffrn_orient_matrix_UB_22      0.0745630000
_diffrn_orient_matrix_UB_23      0.0336128000
_diffrn_orient_matrix_UB_31      0.0729415000
_diffrn_orient_matrix_UB_32      0.0474351000
_diffrn_orient_matrix_UB_33      -0.0951766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3575
_reflns_number_total             3602
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.117a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0061(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3602
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+1.3750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.85661(2) 0.46798(2) 1.10981(2) 0.01573(11) Uani 1 1 d . . . . .
O1 O 0.53486(16) 0.30159(8) 0.81566(11) 0.0151(3) Uani 1 1 d . . . . .
N1 N 0.94602(19) 0.35812(9) 0.89320(13) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.6640(2) 0.41659(11) 1.05520(15) 0.0137(3) Uani 1 1 d . . . . .
O2 O 1.02711(16) 0.32902(8) 0.79872(11) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.5193(2) 0.42394(12) 1.11150(16) 0.0159(4) Uani 1 1 d . . . . .
H2 H 0.518325 0.451593 1.179873 0.019 Uiso 1 1 calc R U . . .
O3 O 0.66171(18) 0.48872(10) 0.37752(11) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.3754(2) 0.38988(12) 1.06559(17) 0.0181(4) Uani 1 1 d . . . . .
H3 H 0.276786 0.395208 1.103981 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3709(2) 0.34849(12) 0.96588(16) 0.0169(4) Uani 1 1 d . . . . .
H4 H 0.271977 0.326087 0.935572 0.020 Uiso 1 1 calc R U . . .
C5 C 0.5179(2) 0.34154(11) 0.91291(15) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.6651(2) 0.37485(11) 0.95631(15) 0.0132(3) Uani 1 1 d . . . . .
C7 C 0.7894(2) 0.35454(11) 0.87843(15) 0.0125(3) Uani 1 1 d . . . . .
C8 C 0.7031(2) 0.31516(11) 0.78006(15) 0.0130(3) Uani 1 1 d . . . . .
C9 C 0.7906(2) 0.23511(11) 0.76547(16) 0.0152(4) Uani 1 1 d . . . . .
H9A H 0.746349 0.208130 0.697976 0.018 Uiso 1 1 calc R U . . .
H9B H 0.771224 0.199979 0.829322 0.018 Uiso 1 1 calc R U . . .
C10 C 0.9767(2) 0.24974(11) 0.75632(15) 0.0143(4) Uani 1 1 d . . . . .
C11 C 1.0281(2) 0.25230(12) 0.63762(16) 0.0178(4) Uani 1 1 d . . . . .
H11A H 1.005898 0.200383 0.602587 0.027 Uiso 1 1 calc R U . . .
H11B H 1.145703 0.264076 0.636020 0.027 Uiso 1 1 calc R U . . .
H11C H 0.966044 0.294078 0.597576 0.027 Uiso 1 1 calc R U . . .
C12 C 1.0742(3) 0.18651(12) 0.82279(16) 0.0199(4) Uani 1 1 d . . . . .
H12A H 1.040744 0.133020 0.797637 0.030 Uiso 1 1 calc R U . . .
H12B H 1.052590 0.192267 0.901250 0.030 Uiso 1 1 calc R U . . .
H12C H 1.191681 0.193798 0.812000 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6930(2) 0.36574(11) 0.67630(15) 0.0133(3) Uani 1 1 d . . . . .
C14 C 0.7713(2) 0.43909(12) 0.66763(15) 0.0155(4) Uani 1 1 d . . . . .
H14 H 0.830143 0.460473 0.730078 0.019 Uiso 1 1 calc R U . . .
C15 C 0.7652(2) 0.48205(12) 0.56871(16) 0.0163(4) Uani 1 1 d . . . . .
H15 H 0.821127 0.531701 0.563758 0.020 Uiso 1 1 calc R U . . .
C16 C 0.6767(2) 0.45163(12) 0.47737(15) 0.0148(4) Uani 1 1 d . . . . .
C17 C 0.5948(2) 0.37839(12) 0.48587(15) 0.0150(4) Uani 1 1 d . . . . .
H17 H 0.532777 0.357867 0.424231 0.018 Uiso 1 1 calc R U . . .
C18 C 0.6040(2) 0.33586(11) 0.58359(15) 0.0147(4) Uani 1 1 d . . . . .
H18 H 0.549441 0.285830 0.588166 0.018 Uiso 1 1 calc R U . . .
C19 C 0.7513(3) 0.56137(13) 0.36460(17) 0.0201(4) Uani 1 1 d . . . . .
H19A H 0.727982 0.583014 0.290552 0.030 Uiso 1 1 calc R U . . .
H19B H 0.869065 0.550597 0.374544 0.030 Uiso 1 1 calc R U . . .
H19C H 0.718263 0.600309 0.419838 0.030 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 C1 1.8872(19) . ?
O1 C5 1.368(2) . ?
O1 C8 1.473(2) . ?
N1 O2 1.4319(19) . ?
N1 C7 1.284(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.388(3) . ?
O2 C10 1.474(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(3) . ?
O3 C16 1.362(2) . ?
O3 C19 1.429(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.407(3) . ?
C6 C7 1.454(3) . ?
C7 C8 1.512(2) . ?
C8 C9 1.530(3) . ?
C8 C13 1.516(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.546(3) . ?
C10 C11 1.517(3) . ?
C10 C12 1.533(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.389(3) . ?
C13 C18 1.406(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.398(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(3) . ?
C16 C17 1.400(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C8 107.83(14) . . ?
C7 N1 O2 111.22(14) . . ?
C2 C1 Br1 119.84(14) . . ?
C6 C1 Br1 119.82(14) . . ?
C6 C1 C2 120.27(17) . . ?
N1 O2 C10 116.96(13) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.84(18) . . ?
C3 C2 H2 120.6 . . ?
C16 O3 C19 117.18(15) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.66(18) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.82(18) . . ?
C5 C4 H4 121.6 . . ?
O1 C5 C4 124.06(17) . . ?
O1 C5 C6 113.65(16) . . ?
C4 C5 C6 122.28(18) . . ?
C1 C6 C5 119.12(17) . . ?
C1 C6 C7 135.12(17) . . ?
C5 C6 C7 105.77(16) . . ?
N1 C7 C6 127.91(17) . . ?
N1 C7 C8 124.01(16) . . ?
C6 C7 C8 107.45(15) . . ?
O1 C8 C7 104.20(14) . . ?
O1 C8 C9 110.11(15) . . ?
O1 C8 C13 108.07(14) . . ?
C7 C8 C9 105.52(15) . . ?
C7 C8 C13 114.86(15) . . ?
C13 C8 C9 113.65(15) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.51(15) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
O2 C10 C9 112.21(14) . . ?
O2 C10 C11 102.82(15) . . ?
O2 C10 C12 107.75(15) . . ?
C11 C10 C9 112.53(15) . . ?
C11 C10 C12 111.18(16) . . ?
C12 C10 C9 110.08(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C8 123.10(16) . . ?
C14 C13 C18 118.52(17) . . ?
C18 C13 C8 118.36(17) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.23(17) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.62(18) . . ?
C16 C15 H15 120.2 . . ?
O3 C16 C15 124.46(18) . . ?
O3 C16 C17 115.97(17) . . ?
C15 C16 C17 119.57(18) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.25(17) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.79(18) . . ?
C17 C18 H18 119.6 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br1 C1 C2 C3 175.71(14) . . . . ?
Br1 C1 C6 C5 -175.67(13) . . . . ?
Br1 C1 C6 C7 4.3(3) . . . . ?
O1 C5 C6 C1 -179.67(16) . . . . ?
O1 C5 C6 C7 0.4(2) . . . . ?
O1 C8 C9 C10 -166.27(14) . . . . ?
O1 C8 C13 C14 122.32(18) . . . . ?
O1 C8 C13 C18 -59.5(2) . . . . ?
N1 O2 C10 C9 36.6(2) . . . . ?
N1 O2 C10 C11 157.79(14) . . . . ?
N1 O2 C10 C12 -84.70(18) . . . . ?
N1 C7 C8 O1 161.59(17) . . . . ?
N1 C7 C8 C9 45.6(2) . . . . ?
N1 C7 C8 C13 -80.4(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C6 C7 N1 15.1(4) . . . . ?
C1 C6 C7 C8 -173.8(2) . . . . ?
O2 N1 C7 C6 176.91(17) . . . . ?
O2 N1 C7 C8 7.1(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
O3 C16 C17 C18 179.38(17) . . . . ?
C3 C4 C5 O1 178.75(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 179.64(17) . . . . ?
C5 O1 C8 C7 10.17(18) . . . . ?
C5 O1 C8 C9 122.91(16) . . . . ?
C5 O1 C8 C13 -112.43(16) . . . . ?
C5 C6 C7 N1 -164.95(19) . . . . ?
C5 C6 C7 C8 6.2(2) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C7 C8 O1 -9.98(19) . . . . ?
C6 C7 C8 C9 -125.98(16) . . . . ?
C6 C7 C8 C13 108.04(17) . . . . ?
C7 N1 O2 C10 -51.6(2) . . . . ?
C7 C8 C9 C10 -54.38(19) . . . . ?
C7 C8 C13 C14 6.5(3) . . . . ?
C7 C8 C13 C18 -175.32(16) . . . . ?
C8 O1 C5 C4 173.79(17) . . . . ?
C8 O1 C5 C6 -6.9(2) . . . . ?
C8 C9 C10 O2 18.4(2) . . . . ?
C8 C9 C10 C11 -96.97(18) . . . . ?
C8 C9 C10 C12 138.42(16) . . . . ?
C8 C13 C14 C15 176.95(18) . . . . ?
C8 C13 C18 C17 -178.10(17) . . . . ?
C9 C8 C13 C14 -115.2(2) . . . . ?
C9 C8 C13 C18 63.0(2) . . . . ?
C13 C8 C9 C10 72.34(19) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C14 C15 C16 O3 179.53(18) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 1.0(3) . . . . ?
C18 C13 C14 C15 -1.2(3) . . . . ?
C19 O3 C16 C15 3.8(3) . . . . ?
C19 O3 C16 C17 -176.64(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.069
_oxdiff_exptl_absorpt_empirical_full_min 0.465
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, Ethyl Acetate'
_chemical_properties_physical    Heat-sensitive
