# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_jwmvi60a
_database_code_depnum_ccdc_archive 'CCDC 2022413'
loop_
_audit_author_name
_audit_author_address
'Mairi Haddow'
;Heriot Watt University
United Kingdom
;
_audit_update_record             
;
2020-08-10 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H25 Br N2 O5'
_chemical_formula_sum            'C24 H25 Br N2 O5'
_chemical_formula_weight         501.37
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.9355(4)
_cell_length_b                   9.9998(8)
_cell_length_c                   44.492(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2195.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.36
_cell_measurement_theta_min      4.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            15300
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.358
_diffrn_reflns_theta_max         66.358
_diffrn_reflns_theta_min         3.974
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus rotating anode'
_diffrn_source_current           60.0
_diffrn_source_power             2.7
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3679
_reflns_number_total             3778
_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 1.3 (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    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         1.004
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.229
_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)+(0.0161P)²+7.3549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1220
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.99 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C)
;
_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 -0.34991(15) 0.50408(8) 0.51619(2) 0.0294(2) Uani 1 1 d . . . . .
N1 N 0.4178(13) 0.4170(6) 0.26559(13) 0.0279(14) Uani 1 1 d D . . . .
H1A H 0.355(18) 0.408(8) 0.2865(8) 0.033 Uiso 1 1 d D U . . .
H1B H 0.294(13) 0.450(7) 0.2498(13) 0.033 Uiso 1 1 d D U . . .
N2 N 0.7670(13) 0.0912(6) 0.38844(13) 0.0223(12) Uani 1 1 d . . . . .
H2 H 0.955(19) 0.073(8) 0.3920(17) 0.027 Uiso 1 1 d . U . . .
O1 O 1.0074(11) 0.2192(5) 0.19307(11) 0.0296(11) Uani 1 1 d . . . . .
O2 O 0.4376(11) 0.3112(5) 0.32014(11) 0.0278(12) Uani 1 1 d . . . . .
O3 O 0.5418(11) 0.3486(5) 0.40555(11) 0.0278(11) Uani 1 1 d . . . . .
O4 O 0.6261(13) 0.5691(5) 0.40680(11) 0.0316(12) Uani 1 1 d . . . . .
O5 O 0.3424(12) 0.0250(5) 0.40067(10) 0.0335(12) Uani 1 1 d . . . . .
C1 C 0.8162(17) 0.2487(7) 0.16867(16) 0.0292(17) Uani 1 1 d . . . . .
C2 C 0.6600(18) 0.3731(7) 0.17601(16) 0.0304(17) Uani 1 1 d . . . . .
H2A H 0.601273 0.430607 0.160310 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6037(15) 0.4031(7) 0.20430(16) 0.0262(16) Uani 1 1 d . . . . .
H3 H 0.496630 0.479488 0.208777 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7059(15) 0.3189(7) 0.22876(15) 0.0242(15) Uani 1 1 d . . . . .
C5 C 0.6151(15) 0.3293(6) 0.25887(15) 0.0225(14) Uani 1 1 d . . . . .
C6 C 0.7412(15) 0.2492(7) 0.28125(16) 0.0216(14) Uani 1 1 d . . . . .
C7 C 0.9569(16) 0.1673(7) 0.27296(15) 0.0256(16) Uani 1 1 d . . . . .
H7 H 1.046060 0.116792 0.288098 0.031 Uiso 1 1 calc R U . . .
C8 C 1.0462(14) 0.1564(7) 0.24382(16) 0.0241(15) Uani 1 1 d . . . . .
H8 H 1.193736 0.099517 0.238857 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9154(15) 0.2307(7) 0.22179(15) 0.0237(16) Uani 1 1 d . . . . .
C10 C 0.982(2) 0.2631(9) 0.14053(17) 0.040(2) Uani 1 1 d . . . . .
H10A H 1.119169 0.332686 0.143461 0.060 Uiso 1 1 calc R U . . .
H10B H 0.863258 0.288120 0.123775 0.060 Uiso 1 1 calc R U . . .
H10C H 1.071111 0.177954 0.135984 0.060 Uiso 1 1 calc R U . . .
C11 C 0.629(2) 0.1282(7) 0.16585(18) 0.0371(19) Uani 1 1 d . . . . .
H11A H 0.736945 0.047266 0.162712 0.056 Uiso 1 1 calc R U . . .
H11B H 0.506480 0.141094 0.148731 0.056 Uiso 1 1 calc R U . . .
H11C H 0.521904 0.118781 0.184307 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6486(16) 0.2528(6) 0.31270(14) 0.0220(14) Uani 1 1 d . . . . .
C13 C 0.8109(15) 0.1813(7) 0.33682(14) 0.0241(15) Uani 1 1 d . . . . .
H13A H 0.996567 0.218632 0.337451 0.029 Uiso 1 1 calc R U . . .
H13B H 0.824704 0.085199 0.331704 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6793(16) 0.1963(6) 0.36770(14) 0.0226(14) Uani 1 1 d . . . . .
H14 H 0.479342 0.186010 0.364889 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7276(16) 0.3339(7) 0.38083(15) 0.0260(16) Uani 1 1 d . . . . .
H15A H 0.916928 0.342150 0.387947 0.031 Uiso 1 1 calc R U . . .
H15B H 0.694115 0.403637 0.365491 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5044(15) 0.4729(7) 0.41597(15) 0.0254(16) Uani 1 1 d . . . . .
C17 C 0.2927(14) 0.4762(7) 0.44000(14) 0.0222(15) Uani 1 1 d . . . . .
C18 C 0.2116(17) 0.6006(7) 0.45090(17) 0.0288(18) Uani 1 1 d . . . . .
H18 H 0.289288 0.680133 0.443001 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0180(17) 0.6078(7) 0.47318(17) 0.0257(17) Uani 1 1 d . . . . .
H19 H -0.038470 0.692464 0.480591 0.031 Uiso 1 1 calc R U . . .
C20 C -0.0927(12) 0.4933(8) 0.48462(14) 0.0249(13) Uani 1 1 d . . . . .
C21 C -0.0202(19) 0.3681(7) 0.47390(17) 0.0288(18) Uani 1 1 d . . . . .
H21 H -0.101308 0.289543 0.481841 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1719(17) 0.3601(6) 0.45150(15) 0.0238(15) Uani 1 1 d . . . . .
H22 H 0.222894 0.275163 0.443788 0.029 Uiso 1 1 calc R U . . .
C23 C 0.5896(13) 0.0141(8) 0.40350(13) 0.0233(14) Uani 1 1 d . . . . .
C24 C 0.7105(15) -0.0902(8) 0.42384(16) 0.0282(17) Uani 1 1 d . . . . .
H24A H 0.652613 -0.073661 0.444575 0.042 Uiso 1 1 calc R U . . .
H24B H 0.908600 -0.085949 0.422671 0.042 Uiso 1 1 calc R U . . .
H24C H 0.649057 -0.179098 0.417519 0.042 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 C20 1.896(6) . ?
N1 H1A 0.986(14) . ?
N1 H1B 0.988(14) . ?
N1 C5 1.344(9) . ?
N2 H2 0.96(9) . ?
N2 C14 1.464(9) . ?
N2 C23 1.345(9) . ?
O1 C1 1.468(9) . ?
O1 C9 1.361(8) . ?
O2 C12 1.239(9) . ?
O3 C15 1.440(8) . ?
O3 C16 1.340(8) . ?
O4 C16 1.206(9) . ?
O5 C23 1.231(8) . ?
C1 C2 1.499(11) . ?
C1 C10 1.502(11) . ?
C1 C11 1.525(11) . ?
C2 H2A 0.9500 . ?
C2 C3 1.323(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.465(10) . ?
C4 C5 1.416(9) . ?
C4 C9 1.394(10) . ?
C5 C6 1.422(10) . ?
C6 C7 1.393(10) . ?
C6 C12 1.472(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.518(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(9) . ?
C14 H14 1.0000 . ?
C14 C15 1.514(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.495(10) . ?
C17 C18 1.394(10) . ?
C17 C22 1.402(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.367(11) . ?
C20 C21 1.386(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.504(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
H1A N1 H1B 121(7) . . ?
C5 N1 H1A 113(5) . . ?
C5 N1 H1B 120(5) . . ?
C14 N2 H2 122(5) . . ?
C23 N2 H2 116(5) . . ?
C23 N2 C14 122.2(6) . . ?
C9 O1 C1 117.6(6) . . ?
C16 O3 C15 116.5(5) . . ?
O1 C1 C2 109.6(6) . . ?
O1 C1 C10 106.6(7) . . ?
O1 C1 C11 107.0(6) . . ?
C2 C1 C10 112.4(6) . . ?
C2 C1 C11 111.2(7) . . ?
C10 C1 C11 109.7(7) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.2(7) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(7) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 123.4(6) . . ?
C9 C4 C3 117.0(6) . . ?
C9 C4 C5 119.5(6) . . ?
N1 C5 C4 119.2(6) . . ?
N1 C5 C6 121.9(6) . . ?
C4 C5 C6 118.8(7) . . ?
C5 C6 C12 121.1(6) . . ?
C7 C6 C5 118.7(6) . . ?
C7 C6 C12 120.2(6) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 C6 122.8(7) . . ?
C8 C7 H7 118.6 . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.3(7) . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C4 120.6(6) . . ?
O1 C9 C8 117.5(6) . . ?
C8 C9 C4 121.8(6) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C6 121.7(6) . . ?
O2 C12 C13 118.5(6) . . ?
C6 C12 C13 119.8(6) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.4(6) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
N2 C14 C13 111.8(6) . . ?
N2 C14 H14 107.3 . . ?
N2 C14 C15 111.3(6) . . ?
C13 C14 H14 107.3 . . ?
C15 C14 C13 111.7(6) . . ?
C15 C14 H14 107.3 . . ?
O3 C15 C14 106.7(6) . . ?
O3 C15 H15A 110.4 . . ?
O3 C15 H15B 110.4 . . ?
C14 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
O3 C16 C17 111.4(6) . . ?
O4 C16 O3 123.7(6) . . ?
O4 C16 C17 124.9(6) . . ?
C18 C17 C16 118.0(6) . . ?
C18 C17 C22 119.3(6) . . ?
C22 C17 C16 122.7(6) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(7) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(7) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 Br1 119.7(6) . . ?
C19 C20 C21 121.7(6) . . ?
C21 C20 Br1 118.6(6) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.6(7) . . ?
C22 C21 H21 120.7 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.6(6) . . ?
C21 C22 H22 119.7 . . ?
N2 C23 C24 116.1(6) . . ?
O5 C23 N2 122.9(7) . . ?
O5 C23 C24 121.1(7) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.986(14) 1.83(6) 2.649(8) 138(7) . yes

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 C20 C21 C22 -178.3(6) . . . . ?
N1 C5 C6 C7 -175.6(6) . . . . ?
N1 C5 C6 C12 3.9(10) . . . . ?
N2 C14 C15 O3 -68.7(8) . . . . ?
O1 C1 C2 C3 -31.8(10) . . . . ?
O2 C12 C13 C14 -0.6(9) . . . . ?
O3 C16 C17 C18 -173.6(6) . . . . ?
O3 C16 C17 C22 5.5(9) . . . . ?
O4 C16 C17 C18 6.0(11) . . . . ?
O4 C16 C17 C22 -174.9(7) . . . . ?
C1 O1 C9 C4 -27.7(9) . . . . ?
C1 O1 C9 C8 155.3(6) . . . . ?
C1 C2 C3 C4 3.3(12) . . . . ?
C2 C3 C4 C5 -168.0(7) . . . . ?
C2 C3 C4 C9 16.2(11) . . . . ?
C3 C4 C5 N1 2.6(11) . . . . ?
C3 C4 C5 C6 -175.6(7) . . . . ?
C3 C4 C9 O1 -3.7(10) . . . . ?
C3 C4 C9 C8 173.2(7) . . . . ?
C4 C5 C6 C7 2.6(10) . . . . ?
C4 C5 C6 C12 -177.9(6) . . . . ?
C5 C4 C9 O1 -179.7(6) . . . . ?
C5 C4 C9 C8 -2.7(10) . . . . ?
C5 C6 C7 C8 -2.7(11) . . . . ?
C5 C6 C12 O2 9.7(10) . . . . ?
C5 C6 C12 C13 -171.5(6) . . . . ?
C6 C7 C8 C9 0.1(11) . . . . ?
C6 C12 C13 C14 -179.5(6) . . . . ?
C7 C6 C12 O2 -170.8(6) . . . . ?
C7 C6 C12 C13 8.0(10) . . . . ?
C7 C8 C9 O1 179.7(6) . . . . ?
C7 C8 C9 C4 2.7(11) . . . . ?
C9 O1 C1 C2 43.9(8) . . . . ?
C9 O1 C1 C10 165.9(6) . . . . ?
C9 O1 C1 C11 -76.8(8) . . . . ?
C9 C4 C5 N1 178.3(6) . . . . ?
C9 C4 C5 C6 0.1(10) . . . . ?
C10 C1 C2 C3 -150.2(8) . . . . ?
C11 C1 C2 C3 86.3(9) . . . . ?
C12 C6 C7 C8 177.7(7) . . . . ?
C12 C13 C14 N2 158.5(6) . . . . ?
C12 C13 C14 C15 -76.2(8) . . . . ?
C13 C14 C15 O3 165.6(6) . . . . ?
C14 N2 C23 O5 0.9(10) . . . . ?
C14 N2 C23 C24 179.6(6) . . . . ?
C15 O3 C16 O4 -3.7(10) . . . . ?
C15 O3 C16 C17 175.8(6) . . . . ?
C16 O3 C15 C14 -164.8(6) . . . . ?
C16 C17 C18 C19 -179.6(7) . . . . ?
C16 C17 C22 C21 179.3(7) . . . . ?
C17 C18 C19 C20 0.3(12) . . . . ?
C18 C17 C22 C21 -1.7(11) . . . . ?
C18 C19 C20 Br1 177.9(6) . . . . ?
C18 C19 C20 C21 -1.5(11) . . . . ?
C19 C20 C21 C22 1.1(11) . . . . ?
C20 C21 C22 C17 0.5(12) . . . . ?
C22 C17 C18 C19 1.3(11) . . . . ?
C23 N2 C14 C13 -126.8(7) . . . . ?
C23 N2 C14 C15 107.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
