# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_s3br2
_database_code_depnum_ccdc_archive 'CCDC 2289737'
loop_
_audit_author_name
_audit_author_address
'Jan Grzegorz Malecki'
;Institute of Chemistry, University of Silesia, Katowice, Poland
Poland
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_audit_creation_date             2020-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N3 O2, Br'
_chemical_formula_sum            'C20 H18 Br N3 O2'
_chemical_formula_weight         412.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 Br1 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.4985(8)
_cell_length_b                   16.3402(11)
_cell_length_c                   8.5914(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.883(5)
_cell_angle_gamma                90
_cell_volume                     1866.86(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2692
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7450
_cell_measurement_theta_min      3.7730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9246
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.358
_diffrn_reflns_theta_min         3.308
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  45.00   1.00   20.47    --    9.90 -99.00  60.00   30
  2  ω     18.00  45.00   1.00   20.47    --    9.90 -99.00  90.00   27
  3  ω    -88.00  42.00   1.00   20.47    --  -11.62   0.00 -90.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0366160000
_diffrn_orient_matrix_UB_12      0.0305985000
_diffrn_orient_matrix_UB_13      0.0050274000
_diffrn_orient_matrix_UB_21      0.0251116000
_diffrn_orient_matrix_UB_22      0.0269185000
_diffrn_orient_matrix_UB_23      -0.0450286000
_diffrn_orient_matrix_UB_31      -0.0295460000
_diffrn_orient_matrix_UB_32      -0.0150116000
_diffrn_orient_matrix_UB_33      -0.0704605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2682
_reflns_number_total             4428
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.039
_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)+(0.0412P)²+0.9845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1182
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.17984(3) 0.13138(3) 0.37377(4) 0.07679(19) Uani 1 1 d . . . . .
O1 O 0.44461(16) 0.07078(14) 0.6375(2) 0.0502(5) Uani 1 1 d . . . . .
O2 O 0.44939(18) 0.19644(15) 0.5469(3) 0.0635(7) Uani 1 1 d . . . . .
N1 N 0.0247(2) 0.09836(19) 0.7373(3) 0.0575(7) Uani 1 1 d . . . . .
N2 N 0.0041(2) 0.0808(3) 0.8810(4) 0.0964(13) Uani 1 1 d . . . . .
N3 N 0.15819(17) 0.12689(15) 0.8976(3) 0.0409(6) Uani 1 1 d . . . . .
C1 C 0.1159(2) 0.1253(2) 0.7474(3) 0.0502(8) Uani 1 1 d . . . . .
H1 H 0.146443 0.140875 0.662825 0.060 Uiso 1 1 calc R U . . .
C2 C 0.0863(3) 0.0995(3) 0.9754(4) 0.0852(14) Uani 1 1 d . . . . .
H2 H 0.094796 0.094559 1.084767 0.102 Uiso 1 1 calc R U . . .
C3 C 0.2607(2) 0.1557(2) 0.9598(4) 0.0421(7) Uani 1 1 d . . . . .
H3A H 0.274(2) 0.1440(16) 1.066(4) 0.036(8) Uiso 1 1 d . . . . .
H3B H 0.260(2) 0.213(2) 0.952(3) 0.047(9) Uiso 1 1 d . . . . .
C4 C 0.3337(2) 0.12145(17) 0.8625(3) 0.0367(6) Uani 1 1 d . . . . .
C5 C 0.3628(2) 0.1747(2) 0.7593(3) 0.0452(7) Uani 1 1 d . . . . .
H5 H 0.344001 0.229252 0.764576 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4211(2) 0.1515(2) 0.6420(4) 0.0474(8) Uani 1 1 d . . . . .
C7 C 0.4207(2) 0.01537(19) 0.7446(3) 0.0415(7) Uani 1 1 d . . . . .
C8 C 0.4572(2) -0.0638(2) 0.7241(4) 0.0498(8) Uani 1 1 d . . . . .
H8 H 0.492281 -0.074631 0.642218 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4411(2) -0.1234(2) 0.8236(4) 0.0490(8) Uani 1 1 d . . . . .
H9 H 0.464817 -0.175815 0.809394 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3889(2) -0.10836(19) 0.9493(3) 0.0430(7) Uani 1 1 d . . . . .
C11 C 0.3765(3) -0.1720(2) 1.0552(4) 0.0556(9) Uani 1 1 d . . . . .
H11 H 0.401206 -0.223909 1.039287 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3292(3) -0.1587(3) 1.1794(5) 0.0675(11) Uani 1 1 d . . . . .
H12 H 0.320639 -0.201248 1.247753 0.081 Uiso 1 1 calc R U . . .
C13 C 0.2937(3) -0.0813(3) 1.2041(5) 0.0742(12) Uani 1 1 d . . . . .
H13 H 0.262165 -0.072049 1.290556 0.089 Uiso 1 1 calc R U . . .
C14 C 0.3039(3) -0.0181(2) 1.1044(4) 0.0605(9) Uani 1 1 d . . . . .
H14 H 0.279220 0.033282 1.124619 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3509(2) -0.02869(19) 0.9716(3) 0.0391(7) Uani 1 1 d . . . . .
C16 C 0.36615(19) 0.03617(18) 0.8623(3) 0.0366(6) Uani 1 1 d . . . . .
C17 C -0.0500(3) 0.0841(3) 0.5967(5) 0.0800(12) Uani 1 1 d . . . . .
H17A H -0.016098 0.058314 0.518684 0.096 Uiso 1 1 calc R U . . .
H17B H -0.097945 0.044657 0.624028 0.096 Uiso 1 1 calc R U . . .
C18 C -0.1044(3) 0.1503(3) 0.5240(5) 0.0819(14) Uani 1 1 d . . . . .
C19 C -0.0843(5) 0.2277(4) 0.5620(9) 0.188(4) Uani 1 1 d . . . . .
H19A H -0.030999 0.240684 0.641887 0.225 Uiso 1 1 calc R U . . .
H19B H -0.123589 0.269156 0.508840 0.225 Uiso 1 1 calc R U . . .
C20 C -0.1808(4) 0.1263(4) 0.3825(7) 0.139(3) Uani 1 1 d . . . . .
H20A H -0.147330 0.115055 0.294860 0.208 Uiso 1 1 calc R U . . .
H20B H -0.227751 0.170314 0.355360 0.208 Uiso 1 1 calc R U . . .
H20C H -0.216158 0.078296 0.406906 0.208 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 C6 1.359(4) . ?
O1 C7 1.368(3) . ?
O2 C6 1.208(4) . ?
N1 N2 1.342(4) . ?
N1 C1 1.297(4) . ?
N1 C17 1.453(4) . ?
N2 C2 1.294(5) . ?
N3 C1 1.319(3) . ?
N3 C2 1.346(4) . ?
N3 C3 1.473(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3A 0.92(3) . ?
C3 H3B 0.94(3) . ?
C3 C4 1.506(4) . ?
C4 C5 1.347(4) . ?
C4 C16 1.461(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.433(4) . ?
C7 C8 1.406(4) . ?
C7 C16 1.392(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.337(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.409(4) . ?
C10 C11 1.410(4) . ?
C10 C15 1.424(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.352(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.408(4) . ?
C15 C16 1.454(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.394(6) . ?
C18 C19 1.323(7) . ?
C18 C20 1.505(6) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C6 O1 C7 122.7(2) . . ?
N2 N1 C17 120.4(3) . . ?
C1 N1 N2 110.8(3) . . ?
C1 N1 C17 128.7(3) . . ?
C2 N2 N1 103.6(3) . . ?
C1 N3 C2 104.6(3) . . ?
C1 N3 C3 125.7(3) . . ?
C2 N3 C3 129.7(3) . . ?
N1 C1 N3 108.6(3) . . ?
N1 C1 H1 125.7 . . ?
N3 C1 H1 125.7 . . ?
N2 C2 N3 112.4(3) . . ?
N2 C2 H2 123.8 . . ?
N3 C2 H2 123.8 . . ?
N3 C3 H3A 108.1(17) . . ?
N3 C3 H3B 107.0(18) . . ?
N3 C3 C4 110.0(2) . . ?
H3A C3 H3B 106(2) . . ?
C4 C3 H3A 115.6(17) . . ?
C4 C3 H3B 109.5(19) . . ?
C5 C4 C3 114.7(3) . . ?
C5 C4 C16 119.6(3) . . ?
C16 C4 C3 125.5(3) . . ?
C4 C5 H5 118.3 . . ?
C4 C5 C6 123.3(3) . . ?
C6 C5 H5 118.3 . . ?
O1 C6 C5 115.8(3) . . ?
O2 C6 O1 117.9(3) . . ?
O2 C6 C5 126.2(3) . . ?
O1 C7 C8 113.4(3) . . ?
O1 C7 C16 122.8(3) . . ?
C16 C7 C8 123.8(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 C15 120.1(3) . . ?
C11 C10 C15 120.1(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.6(4) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C16 119.1(3) . . ?
C14 C15 C10 116.4(3) . . ?
C14 C15 C16 124.5(3) . . ?
C7 C16 C4 115.5(3) . . ?
C7 C16 C15 116.3(3) . . ?
C15 C16 C4 128.3(3) . . ?
N1 C17 H17A 107.6 . . ?
N1 C17 H17B 107.6 . . ?
H17A C17 H17B 107.0 . . ?
C18 C17 N1 119.0(4) . . ?
C18 C17 H17A 107.6 . . ?
C18 C17 H17B 107.6 . . ?
C17 C18 C20 113.3(5) . . ?
C19 C18 C17 124.2(4) . . ?
C19 C18 C20 122.1(5) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 178.4(3) . . . . ?
O1 C7 C16 C4 1.3(4) . . . . ?
O1 C7 C16 C15 -177.2(2) . . . . ?
N1 N2 C2 N3 -0.9(6) . . . . ?
N1 C17 C18 C19 9.0(9) . . . . ?
N1 C17 C18 C20 -178.5(4) . . . . ?
N2 N1 C1 N3 -0.4(4) . . . . ?
N2 N1 C17 C18 102.0(5) . . . . ?
N3 C3 C4 C5 102.6(3) . . . . ?
N3 C3 C4 C16 -71.6(3) . . . . ?
C1 N1 N2 C2 0.8(5) . . . . ?
C1 N1 C17 C18 -80.3(6) . . . . ?
C1 N3 C2 N2 0.7(5) . . . . ?
C1 N3 C3 C4 -45.3(4) . . . . ?
C2 N3 C1 N1 -0.2(4) . . . . ?
C2 N3 C3 C4 137.1(4) . . . . ?
C3 N3 C1 N1 -178.3(3) . . . . ?
C3 N3 C2 N2 178.7(4) . . . . ?
C3 C4 C5 C6 -171.6(3) . . . . ?
C3 C4 C16 C7 169.8(3) . . . . ?
C3 C4 C16 C15 -12.0(4) . . . . ?
C4 C5 C6 O1 1.3(4) . . . . ?
C4 C5 C6 O2 -179.9(3) . . . . ?
C5 C4 C16 C7 -4.2(4) . . . . ?
C5 C4 C16 C15 174.0(3) . . . . ?
C6 O1 C7 C8 -176.4(3) . . . . ?
C6 O1 C7 C16 3.2(4) . . . . ?
C7 O1 C6 O2 176.6(3) . . . . ?
C7 O1 C6 C5 -4.5(4) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C7 C16 C4 -179.2(3) . . . . ?
C8 C7 C16 C15 2.4(4) . . . . ?
C8 C9 C10 C11 -177.7(3) . . . . ?
C8 C9 C10 C15 0.8(5) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C9 C10 C15 C14 -177.1(3) . . . . ?
C9 C10 C15 C16 0.5(4) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C10 C15 C16 C4 179.8(3) . . . . ?
C10 C15 C16 C7 -2.0(4) . . . . ?
C11 C10 C15 C14 1.4(4) . . . . ?
C11 C10 C15 C16 179.0(3) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
C13 C14 C15 C10 -1.3(5) . . . . ?
C13 C14 C15 C16 -178.7(3) . . . . ?
C14 C15 C16 C4 -2.8(5) . . . . ?
C14 C15 C16 C7 175.4(3) . . . . ?
C15 C10 C11 C12 -0.4(5) . . . . ?
C16 C4 C5 C6 3.0(4) . . . . ?
C16 C7 C8 C9 -1.2(5) . . . . ?
C17 N1 N2 C2 178.9(4) . . . . ?
C17 N1 C1 N3 -178.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.789
####################################################################### 
# 
# 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_m2szbr
_database_code_depnum_ccdc_archive 'CCDC 2289738'
loop_
_audit_author_name
_audit_author_address
'Jan Grzegorz Malecki'
;Institute of Chemistry, University of Silesia, Katowice, Poland
Poland
;
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2024-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N3 O2, Br'
_chemical_formula_sum            'C20 H18 Br N3 O2'
_chemical_formula_weight         412.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 Br1 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_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                   10.7857(16)
_cell_length_b                   14.519(2)
_cell_length_c                   11.7467(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.727(15)
_cell_angle_gamma                90
_cell_volume                     1787.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1817
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.6420
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9181
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.385
_diffrn_reflns_theta_min         3.414
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  19.00   1.00   11.26    --   10.68 -77.00-120.00   25
  2  ω    -22.00  47.00   1.00   11.26    --  -10.84  38.00 -60.00   69
  3  ω    -47.00  58.00   1.00   11.26    --  -10.84  19.00  60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0238354000
_diffrn_orient_matrix_UB_12      0.0365069000
_diffrn_orient_matrix_UB_13      0.0291213000
_diffrn_orient_matrix_UB_21      -0.0500031000
_diffrn_orient_matrix_UB_22      0.0073939000
_diffrn_orient_matrix_UB_23      -0.0504624000
_diffrn_orient_matrix_UB_31      -0.0389993000
_diffrn_orient_matrix_UB_32      -0.0316035000
_diffrn_orient_matrix_UB_33      0.0214598000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2403
_reflns_number_total             4160
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.0121(10)
_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   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      0.973
_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)+(0.0562P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1385
_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:
 C3(H3A,H3B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20)
2.c X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.39649(4) 0.13247(3) 0.06460(4) 0.0576(2) Uani 1 1 d . . . . .
O1 O 0.2205(2) -0.10389(17) -0.4026(2) 0.0467(6) Uani 1 1 d . . . . .
O2 O 0.4027(3) -0.1404(2) -0.4427(3) 0.0813(11) Uani 1 1 d . . . . .
N1 N 0.7013(3) 0.11389(18) -0.1279(3) 0.0396(7) Uani 1 1 d . . . . .
N2 N 0.7149(3) 0.1772(2) -0.2085(3) 0.0552(9) Uani 1 1 d . . . . .
N3 N 0.5133(2) 0.15067(19) -0.2164(3) 0.0387(7) Uani 1 1 d . . . . .
C1 C 0.5815(3) 0.0992(2) -0.1327(3) 0.0433(8) Uani 1 1 d . . . . .
H1 H 0.549451 0.059156 -0.084918 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5980(3) 0.1974(3) -0.2612(4) 0.0532(10) Uani 1 1 d . . . . .
H2 H 0.575747 0.239209 -0.322649 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8123(3) 0.0694(2) -0.0515(3) 0.0470(9) Uani 1 1 d . . . . .
H3A H 0.870501 0.049979 -0.098349 0.056 Uiso 1 1 calc R U . . .
H3B H 0.784374 0.014861 -0.016990 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8814(3) 0.1312(2) 0.0440(3) 0.0451(9) Uani 1 1 d . . . . .
C5 C 1.0063(4) 0.1379(3) 0.0646(5) 0.0678(13) Uani 1 1 d . . . . .
H5A H 1.050537 0.174465 0.125889 0.081 Uiso 1 1 calc R U . . .
H5B H 1.050392 0.106071 0.017887 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8011(5) 0.1786(4) 0.1122(4) 0.0759(13) Uani 1 1 d . . . . .
H6A H 0.753956 0.227156 0.065839 0.114 Uiso 1 1 calc R U . . .
H6B H 0.854592 0.203992 0.182283 0.114 Uiso 1 1 calc R U . . .
H6C H 0.742798 0.135207 0.132651 0.114 Uiso 1 1 calc R U . . .
C7 C 0.3743(3) 0.1514(2) -0.2534(3) 0.0435(9) Uani 1 1 d . . . . .
H7A H 0.347145 0.201208 -0.308737 0.052 Uiso 1 1 calc R U . . .
H7B H 0.339253 0.162665 -0.185889 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3228(3) 0.0619(2) -0.3095(3) 0.0389(8) Uani 1 1 d . . . . .
C9 C 0.1894(3) 0.0425(2) -0.3204(3) 0.0370(8) Uani 1 1 d . . . . .
C10 C 0.1021(3) 0.1037(2) -0.2875(3) 0.0444(9) Uani 1 1 d . . . . .
H10 H 0.130179 0.161200 -0.257172 0.053 Uiso 1 1 calc R U . . .
C11 C -0.0217(3) 0.0800(3) -0.2993(3) 0.0463(9) Uani 1 1 d . . . . .
H11 H -0.077779 0.122314 -0.279449 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0671(3) -0.0071(2) -0.3409(3) 0.0423(8) Uani 1 1 d . . . . .
C13 C -0.1942(3) -0.0343(3) -0.3509(3) 0.0512(10) Uani 1 1 d . . . . .
H13 H -0.251371 0.006764 -0.330348 0.061 Uiso 1 1 calc R U . . .
C14 C -0.2346(4) -0.1195(3) -0.3901(4) 0.0592(12) Uani 1 1 d . . . . .
H14 H -0.318881 -0.136433 -0.395387 0.071 Uiso 1 1 calc R U . . .
C15 C -0.1520(4) -0.1812(3) -0.4221(3) 0.0548(10) Uani 1 1 d . . . . .
H15 H -0.181121 -0.239451 -0.448572 0.066 Uiso 1 1 calc R U . . .
C16 C -0.0275(3) -0.1578(3) -0.4155(3) 0.0482(9) Uani 1 1 d . . . . .
H16 H 0.027494 -0.199659 -0.437939 0.058 Uiso 1 1 calc R U . . .
C17 C 0.0164(3) -0.0703(2) -0.3747(3) 0.0376(8) Uani 1 1 d . . . . .
C18 C 0.1443(3) -0.0414(2) -0.3651(3) 0.0394(8) Uani 1 1 d . . . . .
C19 C 0.3461(3) -0.0850(3) -0.4008(4) 0.0550(10) Uani 1 1 d . . . . .
C20 C 0.3950(3) 0.0001(3) -0.3478(3) 0.0486(9) Uani 1 1 d . . . . .
H20 H 0.481164 0.013096 -0.339501 0.058 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 C18 1.366(4) . ?
O1 C19 1.377(4) . ?
O2 C19 1.186(5) . ?
N1 N2 1.352(4) . ?
N1 C1 1.297(4) . ?
N1 C3 1.464(4) . ?
N2 C2 1.300(4) . ?
N3 C1 1.313(4) . ?
N3 C2 1.341(4) . ?
N3 C7 1.459(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.491(5) . ?
C4 C5 1.314(5) . ?
C4 C6 1.481(6) . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(5) . ?
C8 C9 1.442(4) . ?
C8 C20 1.334(5) . ?
C9 C10 1.414(5) . ?
C9 C18 1.369(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.354(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(5) . ?
C12 C13 1.404(5) . ?
C12 C17 1.406(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.355(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.400(5) . ?
C17 C18 1.420(4) . ?
C19 C20 1.428(5) . ?
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
C18 O1 C19 121.8(3) . . ?
N2 N1 C3 121.3(3) . . ?
C1 N1 N2 110.7(3) . . ?
C1 N1 C3 128.0(3) . . ?
C2 N2 N1 103.5(3) . . ?
C1 N3 C2 105.6(3) . . ?
C1 N3 C7 125.5(3) . . ?
C2 N3 C7 128.8(3) . . ?
N1 C1 N3 108.3(3) . . ?
N1 C1 H1 125.8 . . ?
N3 C1 H1 125.8 . . ?
N2 C2 N3 111.9(3) . . ?
N2 C2 H2 124.1 . . ?
N3 C2 H2 124.1 . . ?
N1 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
N1 C3 C4 112.7(3) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 C6 124.8(4) . . ?
C6 C4 C3 115.7(3) . . ?
C4 C5 H5A 120.0 . . ?
C4 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C8 111.8(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C9 C8 C7 117.8(3) . . ?
C20 C8 C7 123.0(3) . . ?
C20 C8 C9 119.2(3) . . ?
C10 C9 C8 124.6(3) . . ?
C18 C9 C8 117.7(3) . . ?
C18 C9 C10 117.7(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.3(3) . . ?
C11 C12 C17 119.5(3) . . ?
C13 C12 C17 118.1(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.5(4) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C18 117.3(3) . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 C18 122.6(3) . . ?
O1 C18 C9 121.9(3) . . ?
O1 C18 C17 115.2(3) . . ?
C9 C18 C17 122.9(3) . . ?
O1 C19 C20 116.1(3) . . ?
O2 C19 O1 117.4(4) . . ?
O2 C19 C20 126.5(4) . . ?
C8 C20 C19 122.9(3) . . ?
C8 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C19 C20 C8 -4.9(6) . . . . ?
O2 C19 C20 C8 175.3(5) . . . . ?
N1 N2 C2 N3 0.7(4) . . . . ?
N1 C3 C4 C5 -132.6(4) . . . . ?
N1 C3 C4 C6 49.6(4) . . . . ?
N2 N1 C1 N3 0.8(4) . . . . ?
N2 N1 C3 C4 75.3(4) . . . . ?
N3 C7 C8 C9 163.0(3) . . . . ?
N3 C7 C8 C20 -16.2(5) . . . . ?
C1 N1 N2 C2 -0.9(4) . . . . ?
C1 N1 C3 C4 -106.7(4) . . . . ?
C1 N3 C2 N2 -0.2(5) . . . . ?
C1 N3 C7 C8 -67.0(5) . . . . ?
C2 N3 C1 N1 -0.4(4) . . . . ?
C2 N3 C7 C8 110.0(4) . . . . ?
C3 N1 N2 C2 177.4(3) . . . . ?
C3 N1 C1 N3 -177.3(3) . . . . ?
C7 N3 C1 N1 177.2(3) . . . . ?
C7 N3 C2 N2 -177.7(3) . . . . ?
C7 C8 C9 C10 3.4(5) . . . . ?
C7 C8 C9 C18 -176.2(3) . . . . ?
C7 C8 C20 C19 179.8(4) . . . . ?
C8 C9 C10 C11 -179.3(3) . . . . ?
C8 C9 C18 O1 -2.4(5) . . . . ?
C8 C9 C18 C17 176.9(3) . . . . ?
C9 C8 C20 C19 0.7(6) . . . . ?
C9 C10 C11 C12 2.1(6) . . . . ?
C10 C9 C18 O1 177.9(3) . . . . ?
C10 C9 C18 C17 -2.8(5) . . . . ?
C10 C11 C12 C13 178.2(4) . . . . ?
C10 C11 C12 C17 -2.1(5) . . . . ?
C11 C12 C13 C14 -179.1(4) . . . . ?
C11 C12 C17 C16 179.5(3) . . . . ?
C11 C12 C17 C18 -0.3(5) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C12 C17 C18 O1 -177.9(3) . . . . ?
C12 C17 C18 C9 2.8(5) . . . . ?
C13 C12 C17 C16 -0.8(5) . . . . ?
C13 C12 C17 C18 179.4(3) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C15 C16 C17 C18 179.7(3) . . . . ?
C16 C17 C18 O1 2.3(5) . . . . ?
C16 C17 C18 C9 -177.0(3) . . . . ?
C17 C12 C13 C14 1.1(6) . . . . ?
C18 O1 C19 O2 -174.7(4) . . . . ?
C18 O1 C19 C20 5.4(5) . . . . ?
C18 C9 C10 C11 0.3(5) . . . . ?
C19 O1 C18 C9 -1.9(5) . . . . ?
C19 O1 C18 C17 178.7(3) . . . . ?
C20 C8 C9 C10 -177.4(4) . . . . ?
C20 C8 C9 C18 3.0(5) . . . . ?

_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 2.434
_oxdiff_exptl_absorpt_empirical_full_min 0.542
