# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2225593'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-12-10
_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         'C27 H23 N O4'
_chemical_formula_sum            'C27 H23 N O4'
_chemical_formula_weight         425.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7528(2)
_cell_length_b                   10.3009(2)
_cell_length_c                   13.3655(2)
_cell_angle_alpha                71.0100(10)
_cell_angle_beta                 73.2780(10)
_cell_angle_gamma                75.2040(10)
_cell_volume                     1073.74(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      68.38
_cell_measurement_theta_min      5.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9210.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18612
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.375
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3572
_reflns_number_total             3853
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.037
_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)+(0.0345P)²+0.2899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0855
_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 Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C25(H25), C17(H17), C24(H24), C12(H12), C21(H21), C8(H8),
 C18(H18), C20(H20), C9(H9), C19(H19), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O4 O 0.22239(10) 0.20894(8) 0.45787(6) 0.0329(2) Uani 1 1 d . . . . .
O1 O 0.40269(10) 0.11287(8) 0.68124(7) 0.0362(2) Uani 1 1 d . . . . .
O2 O -0.15285(10) 0.47605(9) 0.71243(7) 0.0353(2) Uani 1 1 d . . . . .
N1 N 0.48429(11) 0.31703(10) 0.66218(7) 0.0271(2) Uani 1 1 d . . . . .
O3 O 0.09052(14) 0.07176(9) 0.60829(7) 0.0485(3) Uani 1 1 d . . . . .
C22 C 0.25712(13) 0.47945(11) 0.62907(8) 0.0246(2) Uani 1 1 d . . . . .
C27 C 0.16625(14) 0.61221(11) 0.60523(9) 0.0276(2) Uani 1 1 d . . . . .
H27 H 0.058657 0.626086 0.596731 0.033 Uiso 1 1 calc R U . . .
C5 C 0.06585(13) 0.28603(11) 0.72166(9) 0.0255(2) Uani 1 1 d . . . . .
H5 H 0.080547 0.187649 0.768243 0.031 Uiso 1 1 calc R U . . .
C13 C 0.22219(13) 0.33891(11) 0.64790(8) 0.0246(2) Uani 1 1 d . . . . .
C4 C 0.10212(13) 0.30418(11) 0.60309(9) 0.0262(2) Uani 1 1 d . . . . .
H4 H 0.034266 0.387696 0.563184 0.031 Uiso 1 1 calc R U . . .
C6 C -0.06837(13) 0.38765(11) 0.76932(9) 0.0268(2) Uani 1 1 d . . . . .
C16 C 0.63803(13) 0.19832(11) 0.80674(9) 0.0279(2) Uani 1 1 d . . . . .
C23 C 0.41602(13) 0.46049(11) 0.64054(8) 0.0260(2) Uani 1 1 d . . . . .
C3 C 0.13888(13) 0.17937(11) 0.55994(9) 0.0277(2) Uani 1 1 d . . . . .
C15 C 0.64271(13) 0.25358(12) 0.68619(9) 0.0300(2) Uani 1 1 d . . . . .
H15A H 0.714908 0.323645 0.653326 0.036 Uiso 1 1 calc R U . . .
H15B H 0.689771 0.175818 0.652093 0.036 Uiso 1 1 calc R U . . .
C26 C 0.23571(15) 0.72538(12) 0.59392(9) 0.0319(3) Uani 1 1 d . . . . .
H26 H 0.174768 0.817276 0.577798 0.038 Uiso 1 1 calc R U . . .
C14 C 0.37715(13) 0.23915(11) 0.66501(8) 0.0265(2) Uani 1 1 d . . . . .
C7 C -0.09277(14) 0.37738(12) 0.88572(9) 0.0299(2) Uani 1 1 d . . . . .
C25 C 0.39303(15) 0.70483(12) 0.60601(10) 0.0341(3) Uani 1 1 d . . . . .
H25 H 0.438168 0.783310 0.597866 0.041 Uiso 1 1 calc R U . . .
C17 C 0.76829(15) 0.10182(12) 0.84145(10) 0.0338(3) Uani 1 1 d . . . . .
H17 H 0.856508 0.067870 0.790121 0.041 Uiso 1 1 calc R U . . .
C24 C 0.48649(14) 0.57168(12) 0.62985(9) 0.0316(2) Uani 1 1 d . . . . .
H24 H 0.594049 0.557851 0.638407 0.038 Uiso 1 1 calc R U . . .
C12 C -0.23974(16) 0.44234(14) 0.93829(11) 0.0410(3) Uani 1 1 d . . . . .
H12 H -0.321072 0.493495 0.899080 0.049 Uiso 1 1 calc R U . . .
C21 C 0.50943(15) 0.24425(14) 0.88350(10) 0.0368(3) Uani 1 1 d . . . . .
H21 H 0.419310 0.309935 0.860931 0.044 Uiso 1 1 calc R U . . .
C2 C 0.25573(17) 0.10193(13) 0.40101(10) 0.0376(3) Uani 1 1 d . . . . .
H2A H 0.157943 0.060725 0.416910 0.045 Uiso 1 1 calc R U . . .
H2B H 0.344518 0.026601 0.424714 0.045 Uiso 1 1 calc R U . . .
C8 C 0.02615(16) 0.30528(14) 0.94341(10) 0.0384(3) Uani 1 1 d . . . . .
H8 H 0.126588 0.260547 0.908232 0.046 Uiso 1 1 calc R U . . .
C18 C 0.76968(18) 0.05484(14) 0.95124(12) 0.0444(3) Uani 1 1 d . . . . .
H18 H 0.860116 -0.009800 0.974305 0.053 Uiso 1 1 calc R U . . .
C20 C 0.51126(18) 0.19515(16) 0.99288(11) 0.0464(3) Uani 1 1 d . . . . .
H20 H 0.421852 0.226871 1.044628 0.056 Uiso 1 1 calc R U . . .
C1 C 0.3035(2) 0.17033(15) 0.28257(11) 0.0482(3) Uani 1 1 d . . . . .
H1A H 0.325515 0.101240 0.241914 0.072 Uiso 1 1 calc R U . . .
H1B H 0.401219 0.209526 0.267696 0.072 Uiso 1 1 calc R U . . .
H1C H 0.215164 0.245224 0.260223 0.072 Uiso 1 1 calc R U . . .
C9 C -0.0013(2) 0.29840(17) 1.05235(12) 0.0527(4) Uani 1 1 d . . . . .
H9 H 0.080897 0.250384 1.091505 0.063 Uiso 1 1 calc R U . . .
C19 C 0.64088(19) 0.10117(15) 1.02725(11) 0.0483(3) Uani 1 1 d . . . . .
H19 H 0.642076 0.068402 1.102230 0.058 Uiso 1 1 calc R U . . .
C11 C -0.26707(19) 0.43240(17) 1.04700(13) 0.0540(4) Uani 1 1 d . . . . .
H11 H -0.368433 0.474728 1.083044 0.065 Uiso 1 1 calc R U . . .
C10 C -0.1484(2) 0.36150(18) 1.10377(12) 0.0576(4) Uani 1 1 d . . . . .
H10 H -0.167726 0.355939 1.178601 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C3 1.3257(14) . ?
O4 C2 1.4598(13) . ?
O1 C14 1.2186(14) . ?
O2 C6 1.2179(14) . ?
N1 C23 1.4124(14) . ?
N1 C15 1.4524(14) . ?
N1 C14 1.3669(15) . ?
O3 C3 1.2007(14) . ?
C22 C27 1.3824(15) . ?
C22 C13 1.4824(15) . ?
C22 C23 1.4002(16) . ?
C27 H27 0.9500 . ?
C27 C26 1.3950(16) . ?
C5 H5 1.0000 . ?
C5 C13 1.5480(15) . ?
C5 C4 1.4816(15) . ?
C5 C6 1.5023(15) . ?
C13 C4 1.5116(15) . ?
C13 C14 1.5038(15) . ?
C4 H4 1.0000 . ?
C4 C3 1.5012(14) . ?
C6 C7 1.4800(16) . ?
C16 C15 1.5162(15) . ?
C16 C17 1.3887(16) . ?
C16 C21 1.3866(17) . ?
C23 C24 1.3843(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C26 H26 0.9500 . ?
C26 C25 1.3871(18) . ?
C7 C12 1.3937(17) . ?
C7 C8 1.3871(18) . ?
C25 H25 0.9500 . ?
C25 C24 1.3944(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3903(18) . ?
C24 H24 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.376(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.3862(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.4902(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3867(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.373(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.381(2) . ?
C19 H19 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.376(2) . ?
C10 H10 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
C3 O4 C2 116.75(9) . . ?
C23 N1 C15 126.46(9) . . ?
C14 N1 C23 111.33(9) . . ?
C14 N1 C15 122.09(9) . . ?
C27 C22 C13 132.98(10) . . ?
C27 C22 C23 120.11(10) . . ?
C23 C22 C13 106.91(9) . . ?
C22 C27 H27 120.7 . . ?
C22 C27 C26 118.67(10) . . ?
C26 C27 H27 120.7 . . ?
C13 C5 H5 116.1 . . ?
C4 C5 H5 116.1 . . ?
C4 C5 C13 59.81(7) . . ?
C4 C5 C6 118.59(9) . . ?
C6 C5 H5 116.1 . . ?
C6 C5 C13 118.28(9) . . ?
C22 C13 C5 124.78(9) . . ?
C22 C13 C4 126.55(9) . . ?
C22 C13 C14 105.49(9) . . ?
C4 C13 C5 57.91(7) . . ?
C14 C13 C5 114.79(9) . . ?
C14 C13 C4 121.04(9) . . ?
C5 C4 C13 62.27(7) . . ?
C5 C4 H4 114.1 . . ?
C5 C4 C3 120.10(9) . . ?
C13 C4 H4 114.1 . . ?
C3 C4 C13 122.51(9) . . ?
C3 C4 H4 114.1 . . ?
O2 C6 C5 120.11(10) . . ?
O2 C6 C7 121.74(10) . . ?
C7 C6 C5 118.14(10) . . ?
C17 C16 C15 119.20(10) . . ?
C21 C16 C15 121.95(10) . . ?
C21 C16 C17 118.83(11) . . ?
C22 C23 N1 109.47(9) . . ?
C24 C23 N1 128.61(10) . . ?
C24 C23 C22 121.91(10) . . ?
O4 C3 C4 110.02(9) . . ?
O3 C3 O4 124.88(10) . . ?
O3 C3 C4 124.92(10) . . ?
N1 C15 C16 113.40(9) . . ?
N1 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C27 C26 H26 119.7 . . ?
C25 C26 C27 120.54(11) . . ?
C25 C26 H26 119.7 . . ?
O1 C14 N1 126.00(10) . . ?
O1 C14 C13 127.29(10) . . ?
N1 C14 C13 106.68(9) . . ?
C12 C7 C6 118.71(11) . . ?
C8 C7 C6 121.89(10) . . ?
C8 C7 C12 119.40(12) . . ?
C26 C25 H25 119.2 . . ?
C26 C25 C24 121.55(11) . . ?
C24 C25 H25 119.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.05(12) . . ?
C18 C17 H17 120.0 . . ?
C23 C24 C25 117.23(11) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.02(14) . . ?
C11 C12 H12 120.0 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.56(12) . . ?
C20 C21 H21 119.7 . . ?
O4 C2 H2A 110.2 . . ?
O4 C2 H2B 110.2 . . ?
O4 C2 C1 107.45(10) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.12(13) . . ?
C9 C8 H8 119.9 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.72(13) . . ?
C19 C18 H18 119.6 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.71(13) . . ?
C19 C20 H20 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.83(14) . . ?
C10 C9 H9 120.1 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.11(12) . . ?
C20 C19 H19 120.4 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.37(13) . . ?
C10 C11 H11 119.8 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.23(13) . . ?
C11 C10 H10 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C7 C12 17.97(16) . . . . ?
O2 C6 C7 C8 -161.99(11) . . . . ?
N1 C23 C24 C25 178.70(10) . . . . ?
C22 C27 C26 C25 0.22(17) . . . . ?
C22 C13 C4 C5 -111.91(12) . . . . ?
C22 C13 C4 C3 138.40(11) . . . . ?
C22 C13 C14 O1 -178.60(11) . . . . ?
C22 C13 C14 N1 3.20(11) . . . . ?
C22 C23 C24 C25 -0.58(16) . . . . ?
C27 C22 C13 C5 -46.25(17) . . . . ?
C27 C22 C13 C4 26.87(18) . . . . ?
C27 C22 C13 C14 177.52(11) . . . . ?
C27 C22 C23 N1 -178.68(9) . . . . ?
C27 C22 C23 C24 0.71(16) . . . . ?
C27 C26 C25 C24 -0.11(18) . . . . ?
C5 C13 C4 C3 -109.69(11) . . . . ?
C5 C13 C14 O1 40.14(15) . . . . ?
C5 C13 C14 N1 -138.06(9) . . . . ?
C5 C4 C3 O4 -157.51(10) . . . . ?
C5 C4 C3 O3 27.08(17) . . . . ?
C5 C6 C7 C12 -162.58(10) . . . . ?
C5 C6 C7 C8 17.45(16) . . . . ?
C13 C22 C27 C26 178.93(11) . . . . ?
C13 C22 C23 N1 1.74(11) . . . . ?
C13 C22 C23 C24 -178.86(10) . . . . ?
C13 C5 C4 C3 113.40(11) . . . . ?
C13 C5 C6 O2 74.62(13) . . . . ?
C13 C5 C6 C7 -104.83(11) . . . . ?
C13 C4 C3 O4 -83.07(12) . . . . ?
C13 C4 C3 O3 101.52(14) . . . . ?
C4 C5 C13 C22 114.86(11) . . . . ?
C4 C5 C13 C14 -112.39(10) . . . . ?
C4 C5 C6 O2 5.54(15) . . . . ?
C4 C5 C6 C7 -173.91(9) . . . . ?
C4 C13 C14 O1 -25.97(17) . . . . ?
C4 C13 C14 N1 155.83(9) . . . . ?
C6 C5 C13 C22 6.46(15) . . . . ?
C6 C5 C13 C4 -108.40(11) . . . . ?
C6 C5 C13 C14 139.21(10) . . . . ?
C6 C5 C4 C13 107.89(10) . . . . ?
C6 C5 C4 C3 -138.71(10) . . . . ?
C6 C7 C12 C11 178.79(12) . . . . ?
C6 C7 C8 C9 179.84(12) . . . . ?
C16 C17 C18 C19 1.23(19) . . . . ?
C16 C21 C20 C19 0.6(2) . . . . ?
C23 N1 C15 C16 95.49(13) . . . . ?
C23 N1 C14 O1 179.51(10) . . . . ?
C23 N1 C14 C13 -2.26(12) . . . . ?
C23 C22 C27 C26 -0.51(16) . . . . ?
C23 C22 C13 C5 133.25(10) . . . . ?
C23 C22 C13 C4 -153.63(10) . . . . ?
C23 C22 C13 C14 -2.99(11) . . . . ?
C3 O4 C2 C1 163.10(11) . . . . ?
C15 N1 C23 C22 -175.70(9) . . . . ?
C15 N1 C23 C24 4.96(18) . . . . ?
C15 N1 C14 O1 -4.23(17) . . . . ?
C15 N1 C14 C13 174.00(9) . . . . ?
C15 C16 C17 C18 176.99(11) . . . . ?
C15 C16 C21 C20 -177.83(12) . . . . ?
C26 C25 C24 C23 0.27(17) . . . . ?
C14 N1 C23 C22 0.36(12) . . . . ?
C14 N1 C23 C24 -178.99(11) . . . . ?
C14 N1 C15 C16 -80.17(13) . . . . ?
C14 C13 C4 C5 101.55(11) . . . . ?
C14 C13 C4 C3 -8.14(15) . . . . ?
C7 C12 C11 C10 1.7(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C17 C16 C15 N1 161.70(10) . . . . ?
C17 C16 C21 C20 0.29(18) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C12 C7 C8 C9 -0.13(19) . . . . ?
C12 C11 C10 C9 -0.7(3) . . . . ?
C21 C16 C15 N1 -20.18(16) . . . . ?
C21 C16 C17 C18 -1.18(17) . . . . ?
C21 C20 C19 C18 -0.6(2) . . . . ?
C2 O4 C3 O3 0.55(17) . . . . ?
C2 O4 C3 C4 -174.87(9) . . . . ?
C8 C7 C12 C11 -1.24(19) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?

_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_11
_database_code_depnum_ccdc_archive 'CCDC 2225594'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-12-10
_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         'C27 H22 Br N O5'
_chemical_formula_sum            'C27 H22 Br N O5'
_chemical_formula_weight         520.36
_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   13.2115(3)
_cell_length_b                   14.3699(3)
_cell_length_c                   24.8145(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4710.98(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.706
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1224 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.8476.
The λ/2 correction factor is Not present.
;
_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       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3775
_reflns_number_total             4300
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.052
_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)+(0.0397P)²+1.5452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0764
_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 Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C26(H26), C27(H27), C9(H9), C24(H24), C5(H5), C12(H12), C10(H10),
 C4(H4), C1(H1), C11(H11), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.07271(2) 0.49226(2) 0.41742(2) 0.04023(9) Uani 1 1 d . . . . .
O1 O 0.73579(9) 0.79532(9) 0.44912(5) 0.0304(3) Uani 1 1 d . . . . .
O5 O 0.62794(10) 0.57437(9) 0.30558(5) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.73839(10) 0.88092(9) 0.24825(5) 0.0346(3) Uani 1 1 d . . . . .
O4 O 0.63068(10) 0.69195(10) 0.24636(5) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.56531(10) 0.76447(10) 0.45657(5) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.58031(11) 0.90060(12) 0.27855(6) 0.0466(4) Uani 1 1 d . . . . .
C15 C 0.65325(12) 0.77788(11) 0.42913(6) 0.0225(3) Uani 1 1 d . . . . .
C19 C 0.70383(11) 0.71225(12) 0.33438(6) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.51677(12) 0.75580(11) 0.36785(6) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.48328(12) 0.75104(11) 0.42132(6) 0.0219(3) Uani 1 1 d . . . . .
C22 C 0.79353(12) 0.66191(11) 0.35745(6) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.62897(12) 0.76846(11) 0.36996(6) 0.0223(3) Uani 1 1 d . . . . .
C23 C 0.78184(13) 0.59349(12) 0.39656(7) 0.0261(3) Uani 1 1 d . . . . .
H23 H 0.716556 0.581263 0.410963 0.031 Uiso 1 1 calc R U . . .
C25 C 0.95889(13) 0.56194(12) 0.39314(7) 0.0267(3) Uani 1 1 d . . . . .
C20 C 0.65096(12) 0.65964(12) 0.28975(6) 0.0238(3) Uani 1 1 d . . . . .
C16 C 0.70086(12) 0.81647(12) 0.33176(6) 0.0241(3) Uani 1 1 d . . . . .
H16 H 0.759321 0.847015 0.350262 0.029 Uiso 1 1 calc R U . . .
C26 C 0.97292(13) 0.62985(12) 0.35491(7) 0.0278(4) Uani 1 1 d . . . . .
H26 H 1.038486 0.642350 0.340963 0.033 Uiso 1 1 calc R U . . .
C7 C 0.55839(13) 0.76832(12) 0.51535(6) 0.0253(3) Uani 1 1 d . . . . .
H7A H 0.496705 0.803220 0.525580 0.030 Uiso 1 1 calc R U . . .
H7B H 0.617569 0.802651 0.529626 0.030 Uiso 1 1 calc R U . . .
C6 C 0.55485(12) 0.67313(12) 0.54083(6) 0.0234(3) Uani 1 1 d . . . . .
C27 C 0.88930(12) 0.68005(12) 0.33698(6) 0.0251(3) Uani 1 1 d . . . . .
H27 H 0.897865 0.727132 0.310495 0.030 Uiso 1 1 calc R U . . .
C9 C 0.38307(13) 0.73616(13) 0.43493(7) 0.0276(4) Uani 1 1 d . . . . .
H9 H 0.361735 0.733277 0.471449 0.033 Uiso 1 1 calc R U . . .
C24 C 0.86460(14) 0.54276(13) 0.41485(7) 0.0290(4) Uani 1 1 d . . . . .
H24 H 0.856655 0.496042 0.441605 0.035 Uiso 1 1 calc R U . . .
C17 C 0.66337(13) 0.86937(13) 0.28359(7) 0.0288(4) Uani 1 1 d . . . . .
C5 C 0.47019(13) 0.64561(13) 0.56958(7) 0.0283(4) Uani 1 1 d . . . . .
H5 H 0.414150 0.686637 0.572904 0.034 Uiso 1 1 calc R U . . .
C12 C 0.44749(13) 0.74602(13) 0.32639(7) 0.0288(4) Uani 1 1 d . . . . .
H12 H 0.468636 0.749990 0.289868 0.035 Uiso 1 1 calc R U . . .
C10 C 0.31489(12) 0.72561(14) 0.39253(8) 0.0317(4) Uani 1 1 d . . . . .
H10 H 0.245455 0.714993 0.400346 0.038 Uiso 1 1 calc R U . . .
C4 C 0.46673(15) 0.55832(14) 0.59361(8) 0.0354(4) Uani 1 1 d . . . . .
H4 H 0.408865 0.540185 0.613763 0.042 Uiso 1 1 calc R U . . .
C1 C 0.63607(13) 0.61192(13) 0.53567(7) 0.0309(4) Uani 1 1 d . . . . .
H1 H 0.694523 0.630150 0.516035 0.037 Uiso 1 1 calc R U . . .
C11 C 0.34590(13) 0.73022(14) 0.33915(7) 0.0332(4) Uani 1 1 d . . . . .
H11 H 0.297713 0.722568 0.311086 0.040 Uiso 1 1 calc R U . . .
C3 C 0.54757(19) 0.49780(13) 0.58817(8) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.545215 0.437951 0.604387 0.045 Uiso 1 1 calc R U . . .
C21 C 0.56649(16) 0.52056(14) 0.26854(9) 0.0397(5) Uani 1 1 d . . . . .
H21A H 0.600894 0.516355 0.233639 0.060 Uiso 1 1 calc R U . . .
H21B H 0.500739 0.551070 0.263833 0.060 Uiso 1 1 calc R U . . .
H21C H 0.556285 0.457874 0.283119 0.060 Uiso 1 1 calc R U . . .
C2 C 0.63173(16) 0.52482(15) 0.55906(8) 0.0379(4) Uani 1 1 d . . . . .
H2 H 0.687050 0.483142 0.555097 0.046 Uiso 1 1 calc R U . . .
C18 C 0.70978(17) 0.92783(17) 0.19882(8) 0.0479(5) Uani 1 1 d . . . . .
H18A H 0.767187 0.927725 0.173807 0.072 Uiso 1 1 calc R U . . .
H18B H 0.690412 0.992162 0.206912 0.072 Uiso 1 1 calc R U . . .
H18C H 0.652406 0.895319 0.182323 0.072 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 C25 1.9044(16) . ?
O1 C15 1.224(2) . ?
O5 C20 1.322(2) . ?
O5 C21 1.450(2) . ?
O3 C17 1.334(2) . ?
O3 C18 1.450(2) . ?
O4 C20 1.203(2) . ?
N1 C15 1.360(2) . ?
N1 C8 1.406(2) . ?
N1 C7 1.4625(19) . ?
O2 C17 1.192(2) . ?
C15 C14 1.509(2) . ?
C19 C22 1.502(2) . ?
C19 C14 1.552(2) . ?
C19 C20 1.512(2) . ?
C19 C16 1.500(2) . ?
C13 C8 1.400(2) . ?
C13 C14 1.494(2) . ?
C13 C12 1.384(2) . ?
C8 C9 1.383(2) . ?
C22 C23 1.390(2) . ?
C22 C27 1.388(2) . ?
C14 C16 1.509(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(2) . ?
C25 C26 1.373(3) . ?
C25 C24 1.385(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.501(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.392(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.508(2) . ?
C6 C5 1.384(2) . ?
C6 C1 1.393(2) . ?
C27 H27 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C24 H24 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.398(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C11 H11 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.382(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 H2 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C20 O5 C21 115.77(14) . . ?
C17 O3 C18 114.86(15) . . ?
C15 N1 C8 111.49(13) . . ?
C15 N1 C7 123.17(13) . . ?
C8 N1 C7 125.27(13) . . ?
O1 C15 N1 125.96(15) . . ?
O1 C15 C14 127.01(15) . . ?
N1 C15 C14 107.02(13) . . ?
C22 C19 C14 122.45(13) . . ?
C22 C19 C20 113.76(14) . . ?
C20 C19 C14 112.49(13) . . ?
C16 C19 C22 121.21(14) . . ?
C16 C19 C14 59.23(10) . . ?
C16 C19 C20 117.10(13) . . ?
C8 C13 C14 106.63(13) . . ?
C12 C13 C8 119.36(15) . . ?
C12 C13 C14 133.97(15) . . ?
C13 C8 N1 109.83(14) . . ?
C9 C8 N1 127.39(14) . . ?
C9 C8 C13 122.78(15) . . ?
C23 C22 C19 121.27(14) . . ?
C27 C22 C19 119.30(14) . . ?
C27 C22 C23 119.31(15) . . ?
C15 C14 C19 117.69(13) . . ?
C13 C14 C15 104.82(12) . . ?
C13 C14 C19 123.27(13) . . ?
C13 C14 C16 131.15(14) . . ?
C16 C14 C15 115.88(14) . . ?
C16 C14 C19 58.64(10) . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.76(16) . . ?
C24 C23 H23 119.6 . . ?
C26 C25 Br1 119.05(13) . . ?
C26 C25 C24 122.10(16) . . ?
C24 C25 Br1 118.85(13) . . ?
O5 C20 C19 110.61(13) . . ?
O4 C20 O5 124.92(16) . . ?
O4 C20 C19 124.45(16) . . ?
C19 C16 C14 62.13(11) . . ?
C19 C16 H16 113.5 . . ?
C19 C16 C17 123.31(14) . . ?
C14 C16 H16 113.5 . . ?
C17 C16 C14 121.62(14) . . ?
C17 C16 H16 113.5 . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.80(15) . . ?
C27 C26 H26 120.6 . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
N1 C7 C6 112.70(13) . . ?
H7A C7 H7B 107.8 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C5 C6 C7 120.02(15) . . ?
C5 C6 C1 119.30(17) . . ?
C1 C6 C7 120.68(15) . . ?
C22 C27 C26 120.59(16) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C8 C9 H9 121.6 . . ?
C8 C9 C10 116.83(15) . . ?
C10 C9 H9 121.6 . . ?
C23 C24 H24 120.8 . . ?
C25 C24 C23 118.43(16) . . ?
C25 C24 H24 120.8 . . ?
O3 C17 C16 109.97(14) . . ?
O2 C17 O3 124.62(16) . . ?
O2 C17 C16 125.31(16) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.36(17) . . ?
C4 C5 H5 119.8 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.88(16) . . ?
C11 C12 H12 120.6 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.64(16) . . ?
C11 C10 H10 119.2 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.00(18) . . ?
C3 C4 H4 120.0 . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.11(17) . . ?
C2 C1 H1 119.9 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.50(16) . . ?
C10 C11 H11 119.8 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.70(18) . . ?
C2 C3 H3 120.2 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C2 C3 120.52(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C25 C26 C27 179.46(12) . . . . ?
Br1 C25 C24 C23 -179.50(13) . . . . ?
O1 C15 C14 C19 43.8(2) . . . . ?
O1 C15 C14 C13 -174.96(17) . . . . ?
O1 C15 C14 C16 -22.7(3) . . . . ?
N1 C15 C14 C19 -136.98(14) . . . . ?
N1 C15 C14 C13 4.26(17) . . . . ?
N1 C15 C14 C16 156.52(14) . . . . ?
N1 C8 C9 C10 179.37(17) . . . . ?
N1 C7 C6 C5 -116.84(16) . . . . ?
N1 C7 C6 C1 63.0(2) . . . . ?
C15 N1 C8 C13 -0.19(19) . . . . ?
C15 N1 C8 C9 -179.51(17) . . . . ?
C15 N1 C7 C6 -101.48(18) . . . . ?
C15 C14 C16 C19 108.01(15) . . . . ?
C15 C14 C16 C17 -138.17(16) . . . . ?
C19 C22 C23 C24 175.39(15) . . . . ?
C19 C22 C27 C26 -175.51(15) . . . . ?
C19 C14 C16 C17 113.82(18) . . . . ?
C19 C16 C17 O3 -86.05(19) . . . . ?
C19 C16 C17 O2 97.3(2) . . . . ?
C13 C8 C9 C10 0.1(3) . . . . ?
C13 C14 C16 C19 -108.70(19) . . . . ?
C13 C14 C16 C17 5.1(3) . . . . ?
C13 C12 C11 C10 0.8(3) . . . . ?
C8 N1 C15 O1 176.59(17) . . . . ?
C8 N1 C15 C14 -2.64(18) . . . . ?
C8 N1 C7 C6 81.6(2) . . . . ?
C8 C13 C14 C15 -4.34(17) . . . . ?
C8 C13 C14 C19 134.13(15) . . . . ?
C8 C13 C14 C16 -150.54(17) . . . . ?
C8 C13 C12 C11 -1.0(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C22 C19 C14 C15 4.7(2) . . . . ?
C22 C19 C14 C13 -128.91(16) . . . . ?
C22 C19 C14 C16 109.64(17) . . . . ?
C22 C19 C20 O5 52.63(18) . . . . ?
C22 C19 C20 O4 -129.00(17) . . . . ?
C22 C19 C16 C14 -111.68(15) . . . . ?
C22 C19 C16 C17 137.09(16) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C14 C19 C22 C23 58.4(2) . . . . ?
C14 C19 C22 C27 -125.61(16) . . . . ?
C14 C19 C20 O5 -92.13(16) . . . . ?
C14 C19 C20 O4 86.24(19) . . . . ?
C14 C19 C16 C17 -111.23(17) . . . . ?
C14 C13 C8 N1 2.96(18) . . . . ?
C14 C13 C8 C9 -177.69(16) . . . . ?
C14 C13 C12 C11 176.62(18) . . . . ?
C14 C16 C17 O3 -161.44(15) . . . . ?
C14 C16 C17 O2 22.0(3) . . . . ?
C23 C22 C27 C26 0.6(2) . . . . ?
C25 C26 C27 C22 0.1(2) . . . . ?
C20 C19 C22 C23 -82.46(18) . . . . ?
C20 C19 C22 C27 93.57(18) . . . . ?
C20 C19 C14 C15 145.97(14) . . . . ?
C20 C19 C14 C13 12.3(2) . . . . ?
C20 C19 C14 C16 -109.10(15) . . . . ?
C20 C19 C16 C14 101.27(15) . . . . ?
C20 C19 C16 C17 -10.0(2) . . . . ?
C16 C19 C22 C23 129.47(17) . . . . ?
C16 C19 C22 C27 -54.5(2) . . . . ?
C16 C19 C14 C15 -104.92(16) . . . . ?
C16 C19 C14 C13 121.45(17) . . . . ?
C16 C19 C20 O5 -157.91(14) . . . . ?
C16 C19 C20 O4 20.5(2) . . . . ?
C26 C25 C24 C23 0.8(3) . . . . ?
C7 N1 C15 O1 -0.7(3) . . . . ?
C7 N1 C15 C14 -179.96(14) . . . . ?
C7 N1 C8 C13 177.06(15) . . . . ?
C7 N1 C8 C9 -2.3(3) . . . . ?
C7 C6 C5 C4 -179.40(16) . . . . ?
C7 C6 C1 C2 -179.78(16) . . . . ?
C6 C5 C4 C3 -1.0(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C27 C22 C23 C24 -0.6(2) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C12 C13 C8 N1 -178.86(15) . . . . ?
C12 C13 C8 C9 0.5(3) . . . . ?
C12 C13 C14 C15 177.86(19) . . . . ?
C12 C13 C14 C19 -43.7(3) . . . . ?
C12 C13 C14 C16 31.7(3) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?
C1 C6 C5 C4 0.8(2) . . . . ?
C21 O5 C20 O4 -5.3(3) . . . . ?
C21 O5 C20 C19 173.06(15) . . . . ?
C18 O3 C17 O2 -5.9(3) . . . . ?
C18 O3 C17 C16 177.44(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
