# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_f1
_database_code_depnum_ccdc_archive 'CCDC 2292655'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Br O4'
_chemical_formula_sum            'C18 H15 Br O4'
_chemical_formula_weight         375.21
_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'
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                   5.8727(2)
_cell_length_b                   9.1764(3)
_cell_length_c                   15.6457(5)
_cell_angle_alpha                76.2280(10)
_cell_angle_beta                 82.9630(10)
_cell_angle_gamma                83.7500(10)
_cell_volume                     809.96(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    3.616
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6043
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8024.
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    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21478
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.468
_diffrn_reflns_theta_min         2.923
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_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                2765
_reflns_number_total             2893
_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         0.849
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.063
_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)+(0.0182P)²+0.7806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C11(H11), C18(H18), C3(H3), C2(H2), C14(H14), C16(H16),
 C17(H17), C6(H6), C15(H15)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.39042(5) 0.18991(3) 0.03245(2) 0.04622(11) Uani 1 1 d . . . . .
O3 O 0.4941(2) 0.58635(15) 0.33292(8) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.5968(3) 0.84299(16) 0.20912(10) 0.0374(3) Uani 1 1 d . . . . .
O1 O 0.9398(2) 0.73195(15) 0.17088(10) 0.0360(3) Uani 1 1 d . . . . .
O4 O 0.7301(2) 0.68742(17) 0.40163(10) 0.0350(3) Uani 1 1 d . . . . .
C8 C 0.7300(3) 0.7344(2) 0.21375(12) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.6163(3) 0.4825(2) 0.20795(12) 0.0231(4) Uani 1 1 d . . . . .
C9 C 0.6842(3) 0.5755(2) 0.26666(12) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.824317 0.525675 0.295451 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3367(3) 0.7665(2) 0.51197(12) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.481373 0.802369 0.513791 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1462(3) 0.8137(2) 0.57152(12) 0.0239(4) Uani 1 1 d . . . . .
C5 C 0.7514(3) 0.3542(2) 0.19529(13) 0.0295(4) Uani 1 1 d . . . . .
H5 H 0.890118 0.325592 0.222762 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3311(3) 0.6791(2) 0.45541(12) 0.0267(4) Uani 1 1 d . . . . .
H11 H 0.194371 0.634370 0.452854 0.032 Uiso 1 1 calc R U . . .
C18 C 0.1662(3) 0.9388(2) 0.60565(12) 0.0278(4) Uani 1 1 d . . . . .
H18 H 0.304351 0.988408 0.591460 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4143(3) 0.5239(2) 0.16700(13) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.321738 0.611869 0.175507 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5405(3) 0.6532(2) 0.39694(12) 0.0262(4) Uani 1 1 d . . . . .
C2 C 0.3467(4) 0.4389(2) 0.11412(14) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.208857 0.467479 0.086084 0.039 Uiso 1 1 calc R U . . .
C14 C -0.0569(3) 0.7406(2) 0.59510(12) 0.0272(4) Uani 1 1 d . . . . .
H14 H -0.074432 0.655290 0.572754 0.033 Uiso 1 1 calc R U . . .
C16 C -0.2115(4) 0.9184(2) 0.68287(13) 0.0322(4) Uani 1 1 d . . . . .
H16 H -0.333589 0.954086 0.720359 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4841(4) 0.3110(2) 0.10284(13) 0.0310(4) Uani 1 1 d . . . . .
C17 C -0.0118(4) 0.9916(2) 0.65975(13) 0.0317(4) Uani 1 1 d . . . . .
H17 H 0.003153 1.078397 0.681072 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6847(4) 0.2679(2) 0.14271(14) 0.0350(5) Uani 1 1 d . . . . .
H6 H 0.776420 0.179622 0.134215 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2323(3) 0.7920(2) 0.65081(13) 0.0305(4) Uani 1 1 d . . . . .
H15 H -0.368386 0.740427 0.667343 0.037 Uiso 1 1 calc R U . . .
C7 C 1.0112(4) 0.8739(2) 0.11723(16) 0.0411(5) Uani 1 1 d . . . . .
H7A H 1.140484 0.855218 0.074226 0.062 Uiso 1 1 calc R U . . .
H7B H 1.059058 0.933461 0.155245 0.062 Uiso 1 1 calc R U . . .
H7C H 0.882337 0.929355 0.085859 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.901(2) . ?
O3 C9 1.440(2) . ?
O3 C10 1.360(2) . ?
O2 C8 1.192(2) . ?
O1 C8 1.330(2) . ?
O1 C7 1.446(2) . ?
O4 C10 1.205(2) . ?
C8 C9 1.530(3) . ?
C4 C9 1.506(3) . ?
C4 C5 1.387(3) . ?
C4 C3 1.390(3) . ?
C9 H9 1.0000 . ?
C12 H12 0.9500 . ?
C12 C13 1.462(3) . ?
C12 C11 1.333(3) . ?
C13 C18 1.398(3) . ?
C13 C14 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.473(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C16 C15 1.391(3) . ?
C1 C6 1.376(3) . ?
C17 H17 0.9500 . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C10 O3 C9 114.01(14) . . ?
C8 O1 C7 116.57(15) . . ?
O2 C8 O1 124.92(17) . . ?
O2 C8 C9 125.69(17) . . ?
O1 C8 C9 109.35(15) . . ?
C5 C4 C9 120.65(17) . . ?
C5 C4 C3 119.48(18) . . ?
C3 C4 C9 119.86(16) . . ?
O3 C9 C8 108.53(14) . . ?
O3 C9 C4 107.46(14) . . ?
O3 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
C4 C9 C8 110.84(15) . . ?
C4 C9 H9 110.0 . . ?
C13 C12 H12 116.2 . . ?
C11 C12 H12 116.2 . . ?
C11 C12 C13 127.63(18) . . ?
C18 C13 C12 118.60(17) . . ?
C18 C13 C14 118.32(18) . . ?
C14 C13 C12 123.07(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.13(19) . . ?
C6 C5 H5 119.9 . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.89(18) . . ?
C10 C11 H11 120.6 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.06(18) . . ?
C17 C18 H18 119.5 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.84(18) . . ?
C2 C3 H3 119.6 . . ?
O3 C10 C11 111.13(16) . . ?
O4 C10 O3 122.41(17) . . ?
O4 C10 C11 126.44(18) . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.56(19) . . ?
C1 C2 H2 120.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.32(18) . . ?
C15 C14 H14 119.8 . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.45(19) . . ?
C15 C16 H16 120.3 . . ?
C2 C1 Br1 119.20(16) . . ?
C6 C1 Br1 119.18(16) . . ?
C6 C1 C2 121.60(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.17(19) . . ?
C16 C17 H17 119.9 . . ?
C5 C6 H6 120.3 . . ?
C1 C6 C5 119.39(19) . . ?
C1 C6 H6 120.3 . . ?
C14 C15 C16 120.66(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C6 C5 -178.86(15) . . . . ?
O2 C8 C9 O3 -20.1(3) . . . . ?
O2 C8 C9 C4 97.7(2) . . . . ?
O1 C8 C9 O3 162.05(15) . . . . ?
O1 C8 C9 C4 -80.17(19) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C9 O3 C10 O4 -6.3(3) . . . . ?
C9 O3 C10 C11 172.33(15) . . . . ?
C9 C4 C5 C6 178.60(18) . . . . ?
C9 C4 C3 C2 -178.87(18) . . . . ?
C12 C13 C18 C17 177.69(17) . . . . ?
C12 C13 C14 C15 -179.09(17) . . . . ?
C12 C11 C10 O3 -168.51(17) . . . . ?
C12 C11 C10 O4 10.1(3) . . . . ?
C13 C12 C11 C10 176.06(17) . . . . ?
C13 C18 C17 C16 1.7(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C5 C4 C9 O3 -124.12(18) . . . . ?
C5 C4 C9 C8 117.45(19) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C11 C12 C13 C18 -161.00(19) . . . . ?
C11 C12 C13 C14 18.1(3) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C3 C4 C9 O3 54.9(2) . . . . ?
C3 C4 C9 C8 -63.6(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C3 C2 C1 Br1 178.59(15) . . . . ?
C3 C2 C1 C6 -0.1(3) . . . . ?
C10 O3 C9 C8 -67.12(19) . . . . ?
C10 O3 C9 C4 172.96(14) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
C17 C16 C15 C14 -1.0(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C7 O1 C8 O2 2.1(3) . . . . ?
C7 O1 C8 C9 179.97(17) . . . . ?

_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 2292657'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Br N O5'
_chemical_formula_sum            'C26 H20 Br N O5'
_chemical_formula_weight         506.34
_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      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                   8.7254(5)
_cell_length_b                   11.1393(6)
_cell_length_c                   12.4388(7)
_cell_angle_alpha                85.519(2)
_cell_angle_beta                 73.196(2)
_cell_angle_gamma                87.607(2)
_cell_volume                     1153.59(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    394
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      47.82
_cell_measurement_theta_min      3.99
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0660 after correction.
The Ratio of minimum to maximum transmission is 0.8418.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33437
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        59.000
_diffrn_reflns_theta_max         59.000
_diffrn_reflns_theta_min         3.721
_diffrn_ambient_temperature      294.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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                2919
_reflns_number_total             3315
_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         0.600
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.058
_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)+(0.0365P)²+0.9634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0955
_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:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C26(H26), C9(H9), C25(H25), C22(H22), C11(H11), C10(H10),
 C23(H23), C5(H5), C3(H3), C2(H2), C6(H6), C1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 1.41949(5) 1.04167(4) -0.20812(4) 0.0976(2) Uani 1 1 d . . . . .
O3 O 0.9161(2) 0.67151(17) 0.18592(14) 0.0471(4) Uani 1 1 d . . . . .
O5 O 1.2695(2) 0.50655(16) 0.05600(16) 0.0505(5) Uani 1 1 d . . . . .
O1 O 0.3338(2) 0.70865(18) 0.32304(15) 0.0547(5) Uani 1 1 d . . . . .
O2 O 0.9027(2) 0.5918(2) 0.35952(16) 0.0617(6) Uani 1 1 d . . . . .
N1 N 0.2879(2) 0.68894(19) 0.51552(17) 0.0419(5) Uani 1 1 d . . . . .
O4 O 1.0159(3) 0.4518(2) 0.1207(2) 0.0899(8) Uani 1 1 d . . . . .
C14 C 0.5503(3) 0.6586(2) 0.40951(19) 0.0360(5) Uani 1 1 d . . . . .
C8 C 0.3820(3) 0.6628(2) 0.5895(2) 0.0395(6) Uani 1 1 d . . . . .
C13 C 0.5422(3) 0.6421(2) 0.52874(19) 0.0374(5) Uani 1 1 d . . . . .
C21 C 1.1626(3) 0.7484(2) 0.0638(2) 0.0391(6) Uani 1 1 d . . . . .
C16 C 0.6643(3) 0.6581(2) 0.3113(2) 0.0405(6) Uani 1 1 d . . . . .
H16 H 0.631076 0.674032 0.246895 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3799(3) 0.6884(2) 0.4060(2) 0.0401(6) Uani 1 1 d . . . . .
C18 C 1.0863(3) 0.6501(2) 0.1509(2) 0.0417(6) Uani 1 1 d . . . . .
H18 H 1.127476 0.652508 0.216079 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8367(3) 0.6352(2) 0.2935(2) 0.0418(6) Uani 1 1 d . . . . .
C19 C 1.1159(3) 0.5249(2) 0.1077(2) 0.0449(6) Uani 1 1 d . . . . .
C12 C 0.6535(3) 0.6112(2) 0.5865(2) 0.0471(6) Uani 1 1 d . . . . .
H12 H 0.760026 0.595907 0.547940 0.056 Uiso 1 1 calc R U . . .
C26 C 1.3121(3) 0.7876(2) 0.0603(2) 0.0451(6) Uani 1 1 d . . . . .
H26 H 1.360943 0.756398 0.114064 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3306(3) 0.6559(2) 0.7051(2) 0.0501(7) Uani 1 1 d . . . . .
H9 H 0.223960 0.670285 0.744076 0.060 Uiso 1 1 calc R U . . .
C25 C 1.3898(3) 0.8724(2) -0.0218(2) 0.0524(7) Uani 1 1 d . . . . .
H25 H 1.491967 0.896484 -0.025199 0.063 Uiso 1 1 calc R U . . .
C4 C 0.0744(3) 0.8362(3) 0.5992(2) 0.0478(7) Uani 1 1 d . . . . .
C24 C 1.3148(3) 0.9208(3) -0.0982(2) 0.0531(7) Uani 1 1 d . . . . .
C7 C 0.1168(3) 0.7154(3) 0.5499(2) 0.0501(7) Uani 1 1 d . . . . .
H7A H 0.063764 0.652911 0.605253 0.060 Uiso 1 1 calc R U . . .
H7B H 0.076531 0.713457 0.485065 0.060 Uiso 1 1 calc R U . . .
C22 C 1.0906(3) 0.7982(3) -0.0152(2) 0.0557(7) Uani 1 1 d . . . . .
H22 H 0.989946 0.772560 -0.013783 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6022(4) 0.6035(3) 0.7038(2) 0.0565(7) Uani 1 1 d . . . . .
H11 H 0.675358 0.582561 0.743926 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4446(4) 0.6265(3) 0.7610(2) 0.0576(8) Uani 1 1 d . . . . .
H10 H 0.413897 0.622226 0.839230 0.069 Uiso 1 1 calc R U . . .
C23 C 1.1655(4) 0.8853(3) -0.0959(3) 0.0611(8) Uani 1 1 d . . . . .
H23 H 1.115496 0.919383 -0.147888 0.073 Uiso 1 1 calc R U . . .
C5 C 0.1710(4) 0.9341(3) 0.5605(3) 0.0634(8) Uani 1 1 d . . . . .
H5 H 0.268221 0.925211 0.505640 0.076 Uiso 1 1 calc R U . . .
C3 C -0.0687(4) 0.8515(3) 0.6816(3) 0.0697(9) Uani 1 1 d . . . . .
H3 H -0.135158 0.786314 0.710040 0.084 Uiso 1 1 calc R U . . .
C20 C 1.3138(4) 0.3903(3) 0.0108(3) 0.0642(8) Uani 1 1 d . . . . .
H20A H 1.256389 0.378015 -0.042558 0.096 Uiso 1 1 calc R U . . .
H20B H 1.287553 0.328309 0.070849 0.096 Uiso 1 1 calc R U . . .
H20C H 1.426787 0.387447 -0.025993 0.096 Uiso 1 1 calc R U . . .
C2 C -0.1135(5) 0.9653(5) 0.7222(3) 0.0888(13) Uani 1 1 d . . . . .
H2 H -0.210314 0.975621 0.777254 0.107 Uiso 1 1 calc R U . . .
C6 C 0.1251(5) 1.0461(3) 0.6024(3) 0.0820(11) Uani 1 1 d . . . . .
H6 H 0.191799 1.111537 0.575842 0.098 Uiso 1 1 calc R U . . .
C1 C -0.0172(6) 1.0602(4) 0.6821(4) 0.0902(13) Uani 1 1 d . . . . .
H1 H -0.048355 1.135547 0.709252 0.108 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 C24 1.900(3) . ?
O3 C18 1.436(3) . ?
O3 C17 1.356(3) . ?
O5 C19 1.323(3) . ?
O5 C20 1.445(3) . ?
O1 C15 1.214(3) . ?
O2 C17 1.195(3) . ?
N1 C8 1.408(3) . ?
N1 C15 1.367(3) . ?
N1 C7 1.453(3) . ?
O4 C19 1.186(3) . ?
C14 C13 1.462(3) . ?
C14 C16 1.335(3) . ?
C14 C15 1.522(3) . ?
C8 C13 1.402(3) . ?
C8 C9 1.374(4) . ?
C13 C12 1.384(4) . ?
C21 C18 1.508(3) . ?
C21 C26 1.381(4) . ?
C21 C22 1.382(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.470(4) . ?
C18 H18 0.9800 . ?
C18 C19 1.518(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.393(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C25 H25 0.9300 . ?
C25 C24 1.369(4) . ?
C4 C7 1.511(4) . ?
C4 C5 1.375(4) . ?
C4 C3 1.381(4) . ?
C24 C23 1.369(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C23 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C23 H23 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.388(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C1 1.349(6) . ?
C6 H6 0.9300 . ?
C6 C1 1.359(6) . ?
C1 H1 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
C17 O3 C18 116.98(19) . . ?
C19 O5 C20 116.5(2) . . ?
C8 N1 C7 125.1(2) . . ?
C15 N1 C8 110.7(2) . . ?
C15 N1 C7 124.2(2) . . ?
C13 C14 C15 105.85(19) . . ?
C16 C14 C13 136.8(2) . . ?
C16 C14 C15 117.3(2) . . ?
C13 C8 N1 110.4(2) . . ?
C9 C8 N1 127.0(2) . . ?
C9 C8 C13 122.6(2) . . ?
C8 C13 C14 106.7(2) . . ?
C12 C13 C14 134.0(2) . . ?
C12 C13 C8 119.3(2) . . ?
C26 C21 C18 118.9(2) . . ?
C26 C21 C22 118.6(2) . . ?
C22 C21 C18 122.4(2) . . ?
C14 C16 H16 116.4 . . ?
C14 C16 C17 127.2(2) . . ?
C17 C16 H16 116.4 . . ?
O1 C15 N1 126.3(2) . . ?
O1 C15 C14 127.3(2) . . ?
N1 C15 C14 106.3(2) . . ?
O3 C18 C21 108.7(2) . . ?
O3 C18 H18 109.0 . . ?
O3 C18 C19 107.5(2) . . ?
C21 C18 H18 109.0 . . ?
C21 C18 C19 113.5(2) . . ?
C19 C18 H18 109.0 . . ?
O3 C17 C16 108.9(2) . . ?
O2 C17 O3 123.0(2) . . ?
O2 C17 C16 128.1(2) . . ?
O5 C19 C18 111.0(2) . . ?
O4 C19 O5 124.2(3) . . ?
O4 C19 C18 124.8(2) . . ?
C13 C12 H12 120.8 . . ?
C13 C12 C11 118.4(3) . . ?
C11 C12 H12 120.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.8(2) . . ?
C25 C26 H26 119.6 . . ?
C8 C9 H9 121.5 . . ?
C8 C9 C10 117.0(3) . . ?
C10 C9 H9 121.5 . . ?
C26 C25 H25 120.4 . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
C5 C4 C7 121.8(2) . . ?
C5 C4 C3 118.5(3) . . ?
C3 C4 C7 119.7(3) . . ?
C25 C24 Br1 119.0(2) . . ?
C23 C24 Br1 119.6(2) . . ?
C23 C24 C25 121.4(3) . . ?
N1 C7 C4 113.4(2) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C4 C7 H7A 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C24 C23 C22 118.9(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.8 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 H6 120.0 . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?

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 C24 C23 C22 -179.5(2) . . . . ?
O3 C18 C19 O5 169.09(19) . . . . ?
O3 C18 C19 O4 -12.6(4) . . . . ?
N1 C8 C13 C14 1.2(3) . . . . ?
N1 C8 C13 C12 -178.0(2) . . . . ?
N1 C8 C9 C10 178.8(2) . . . . ?
C14 C13 C12 C11 -180.0(3) . . . . ?
C14 C16 C17 O3 -165.1(2) . . . . ?
C14 C16 C17 O2 15.2(5) . . . . ?
C8 N1 C15 O1 -179.4(2) . . . . ?
C8 N1 C15 C14 0.2(3) . . . . ?
C8 N1 C7 C4 70.5(3) . . . . ?
C8 C13 C12 C11 -1.0(4) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C13 C14 C16 C17 1.6(5) . . . . ?
C13 C14 C15 O1 -179.9(3) . . . . ?
C13 C14 C15 N1 0.5(3) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
C21 C18 C19 O5 48.9(3) . . . . ?
C21 C18 C19 O4 -132.8(3) . . . . ?
C21 C26 C25 C24 2.2(4) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C16 C14 C13 C8 175.9(3) . . . . ?
C16 C14 C13 C12 -5.0(5) . . . . ?
C16 C14 C15 O1 2.4(4) . . . . ?
C16 C14 C15 N1 -177.2(2) . . . . ?
C15 N1 C8 C13 -0.9(3) . . . . ?
C15 N1 C8 C9 179.8(3) . . . . ?
C15 N1 C7 C4 -108.2(3) . . . . ?
C15 C14 C13 C8 -1.1(3) . . . . ?
C15 C14 C13 C12 178.0(3) . . . . ?
C15 C14 C16 C17 178.3(2) . . . . ?
C18 O3 C17 O2 3.1(4) . . . . ?
C18 O3 C17 C16 -176.7(2) . . . . ?
C18 C21 C26 C25 176.4(2) . . . . ?
C18 C21 C22 C23 -177.9(3) . . . . ?
C17 O3 C18 C21 -148.8(2) . . . . ?
C17 O3 C18 C19 88.0(2) . . . . ?
C12 C11 C10 C9 1.2(5) . . . . ?
C26 C21 C18 O3 145.9(2) . . . . ?
C26 C21 C18 C19 -94.6(3) . . . . ?
C26 C21 C22 C23 -0.1(4) . . . . ?
C26 C25 C24 Br1 177.9(2) . . . . ?
C26 C25 C24 C23 -1.1(5) . . . . ?
C9 C8 C13 C14 -179.5(2) . . . . ?
C9 C8 C13 C12 1.3(4) . . . . ?
C25 C24 C23 C22 -0.6(5) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C4 C3 C2 C1 -0.6(5) . . . . ?
C7 N1 C8 C13 -179.8(2) . . . . ?
C7 N1 C8 C9 1.0(4) . . . . ?
C7 N1 C15 O1 -0.5(4) . . . . ?
C7 N1 C15 C14 179.1(2) . . . . ?
C7 C4 C5 C6 176.1(3) . . . . ?
C7 C4 C3 C2 -175.8(3) . . . . ?
C22 C21 C18 O3 -36.3(3) . . . . ?
C22 C21 C18 C19 83.3(3) . . . . ?
C22 C21 C26 C25 -1.6(4) . . . . ?
C5 C4 C7 N1 34.8(4) . . . . ?
C5 C4 C3 C2 1.1(5) . . . . ?
C5 C6 C1 C2 1.0(6) . . . . ?
C3 C4 C7 N1 -148.4(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C3 C2 C1 C6 -0.5(6) . . . . ?
C20 O5 C19 O4 1.7(4) . . . . ?
C20 O5 C19 C18 -180.0(2) . . . . ?

_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_f1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2292656'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-10-03 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 N O5'
_chemical_formula_sum            'C25 H27 N O5'
_chemical_formula_weight         421.47
_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      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                   15.6014(4)
_cell_length_b                   16.7367(4)
_cell_length_c                   17.4153(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4547.41(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8520
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.46
_cell_measurement_theta_min      5.82
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5679
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1341 before and 0.0796 after correction.
The Ratio of minimum to maximum transmission is 0.7541.
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    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47322
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.452
_diffrn_reflns_theta_min         4.632
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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                3371
_reflns_number_total             4157
_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         0.237
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.059
_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)+(0.0654P)²+1.2182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1305
_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:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C17(H17), C25(H25), C21(H21), C24(H24),
 C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
;
_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
O5 O 0.54516(8) 0.42143(6) 0.40736(7) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.43348(8) 0.08353(6) 0.42541(7) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.33664(7) 0.22831(7) 0.49880(7) 0.0343(3) Uani 1 1 d . . . . .
O4 O 0.63705(8) 0.32003(7) 0.38236(7) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.39331(8) 0.16722(7) 0.33064(7) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.42003(9) 0.22963(8) 0.60835(8) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.40547(10) 0.23420(9) 0.53086(9) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.55400(10) 0.25261(8) 0.55796(9) 0.0247(3) Uani 1 1 d . . . . .
C20 C 0.35939(10) 0.13313(9) 0.70136(10) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.49168(10) 0.24681(9) 0.49370(9) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.50594(11) 0.20483(9) 0.41715(9) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.566097 0.187155 0.406931 0.032 Uiso 1 1 calc R U . . .
C5 C 0.49216(11) 0.29258(9) 0.41748(9) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.435308 0.311725 0.398368 0.032 Uiso 1 1 calc R U . . .
C15 C 0.64103(11) 0.26660(9) 0.56140(10) 0.0278(4) Uani 1 1 d . . . . .
H15 H 0.673468 0.274446 0.515855 0.033 Uiso 1 1 calc R U . . .
C3 C 0.43731(11) 0.15160(9) 0.38546(9) 0.0283(4) Uani 1 1 d . . . . .
C19 C 0.35288(10) 0.21488(9) 0.66463(9) 0.0279(4) Uani 1 1 d . . . . .
H19A H 0.296369 0.219921 0.639222 0.034 Uiso 1 1 calc R U . . .
H19B H 0.356136 0.256169 0.705231 0.034 Uiso 1 1 calc R U . . .
C6 C 0.56783(11) 0.34470(9) 0.39993(9) 0.0265(4) Uani 1 1 d . . . . .
C13 C 0.50712(11) 0.24096(9) 0.62561(9) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.68026(11) 0.26897(10) 0.63321(10) 0.0317(4) Uani 1 1 d . . . . .
H16 H 0.739981 0.279419 0.636696 0.038 Uiso 1 1 calc R U . . .
C18 C 0.54563(11) 0.24213(10) 0.69716(10) 0.0311(4) Uani 1 1 d . . . . .
H18 H 0.513364 0.233589 0.742682 0.037 Uiso 1 1 calc R U . . .
C17 C 0.63311(12) 0.25623(10) 0.69984(10) 0.0342(4) Uani 1 1 d . . . . .
H17 H 0.661408 0.257216 0.748137 0.041 Uiso 1 1 calc R U . . .
C25 C 0.33670(11) 0.12333(11) 0.77758(10) 0.0344(4) Uani 1 1 d . . . . .
H25 H 0.319595 0.168468 0.806895 0.041 Uiso 1 1 calc R U . . .
C21 C 0.38510(13) 0.06680(11) 0.65938(12) 0.0414(5) Uani 1 1 d . . . . .
H21 H 0.401183 0.072507 0.607055 0.050 Uiso 1 1 calc R U . . .
C7 C 0.60862(12) 0.48570(10) 0.39273(11) 0.0365(4) Uani 1 1 d . . . . .
C8 C 0.63633(15) 0.48233(12) 0.30967(12) 0.0467(5) Uani 1 1 d . . . . .
H8A H 0.671790 0.434778 0.301364 0.070 Uiso 1 1 calc R U . . .
H8B H 0.669590 0.530276 0.297192 0.070 Uiso 1 1 calc R U . . .
H8C H 0.585594 0.479751 0.276592 0.070 Uiso 1 1 calc R U . . .
C24 C 0.33859(13) 0.04861(13) 0.81171(12) 0.0468(5) Uani 1 1 d . . . . .
H24 H 0.322502 0.042622 0.864011 0.056 Uiso 1 1 calc R U . . .
C2 C 0.36565(14) 0.02818(11) 0.40318(11) 0.0419(5) Uani 1 1 d . . . . .
H2A H 0.366472 0.019591 0.346946 0.050 Uiso 1 1 calc R U . . .
H2B H 0.308958 0.050088 0.417652 0.050 Uiso 1 1 calc R U . . .
C10 C 0.68176(15) 0.47848(13) 0.44889(13) 0.0520(5) Uani 1 1 d . . . . .
H10A H 0.658939 0.474239 0.501158 0.078 Uiso 1 1 calc R U . . .
H10B H 0.718436 0.525857 0.445101 0.078 Uiso 1 1 calc R U . . .
H10C H 0.715451 0.430659 0.436915 0.078 Uiso 1 1 calc R U . . .
C1 C 0.38139(15) -0.04844(11) 0.44398(15) 0.0548(6) Uani 1 1 d . . . . .
H1A H 0.437920 -0.069203 0.429716 0.082 Uiso 1 1 calc R U . . .
H1B H 0.337189 -0.087259 0.429578 0.082 Uiso 1 1 calc R U . . .
H1C H 0.379422 -0.039385 0.499550 0.082 Uiso 1 1 calc R U . . .
C9 C 0.55631(16) 0.56068(11) 0.40788(15) 0.0574(6) Uani 1 1 d . . . . .
H9A H 0.506715 0.561807 0.373359 0.086 Uiso 1 1 calc R U . . .
H9B H 0.591972 0.607937 0.398764 0.086 Uiso 1 1 calc R U . . .
H9C H 0.536507 0.560631 0.461283 0.086 Uiso 1 1 calc R U . . .
C23 C 0.36388(15) -0.01714(12) 0.76959(15) 0.0553(6) Uani 1 1 d . . . . .
H23 H 0.365122 -0.068533 0.792716 0.066 Uiso 1 1 calc R U . . .
C22 C 0.38727(15) -0.00788(12) 0.69402(15) 0.0549(6) Uani 1 1 d . . . . .
H22 H 0.405113 -0.053091 0.665166 0.066 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
O5 C6 1.3383(19) . ?
O5 C7 1.484(2) . ?
O1 C3 1.3364(19) . ?
O1 C2 1.459(2) . ?
O3 C12 1.214(2) . ?
O4 C6 1.196(2) . ?
O2 C3 1.204(2) . ?
N1 C12 1.371(2) . ?
N1 C19 1.456(2) . ?
N1 C13 1.404(2) . ?
C12 C11 1.508(2) . ?
C14 C11 1.486(2) . ?
C14 C15 1.379(2) . ?
C14 C13 1.400(2) . ?
C20 C19 1.514(2) . ?
C20 C25 1.383(2) . ?
C20 C21 1.388(2) . ?
C11 C4 1.523(2) . ?
C11 C5 1.533(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.484(2) . ?
C4 C3 1.498(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.499(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C13 C18 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C7 C8 1.511(3) . ?
C7 C10 1.508(3) . ?
C7 C9 1.520(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C23 1.380(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.487(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C22 1.375(3) . ?
C22 H22 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
C6 O5 C7 120.18(13) . . ?
C3 O1 C2 115.83(14) . . ?
C12 N1 C19 123.58(14) . . ?
C12 N1 C13 111.31(13) . . ?
C13 N1 C19 125.11(14) . . ?
O3 C12 N1 126.50(15) . . ?
O3 C12 C11 127.09(15) . . ?
N1 C12 C11 106.41(13) . . ?
C15 C14 C11 133.48(15) . . ?
C15 C14 C13 120.09(15) . . ?
C13 C14 C11 106.42(14) . . ?
C25 C20 C19 119.69(15) . . ?
C25 C20 C21 118.97(16) . . ?
C21 C20 C19 121.30(15) . . ?
C12 C11 C4 116.19(13) . . ?
C12 C11 C5 116.49(14) . . ?
C14 C11 C12 105.65(13) . . ?
C14 C11 C4 126.43(14) . . ?
C14 C11 C5 128.07(14) . . ?
C4 C11 C5 58.12(10) . . ?
C11 C4 H4 115.4 . . ?
C5 C4 C11 61.25(10) . . ?
C5 C4 H4 115.4 . . ?
C5 C4 C3 119.09(14) . . ?
C3 C4 C11 119.50(14) . . ?
C3 C4 H4 115.4 . . ?
C11 C5 H5 116.4 . . ?
C4 C5 C11 60.62(10) . . ?
C4 C5 H5 116.4 . . ?
C4 C5 C6 117.43(14) . . ?
C6 C5 C11 118.11(14) . . ?
C6 C5 H5 116.4 . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.45(15) . . ?
C16 C15 H15 120.8 . . ?
O1 C3 C4 110.31(14) . . ?
O2 C3 O1 124.90(15) . . ?
O2 C3 C4 124.77(15) . . ?
N1 C19 C20 112.92(13) . . ?
N1 C19 H19A 109.0 . . ?
N1 C19 H19B 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
O5 C6 C5 109.29(14) . . ?
O4 C6 O5 126.49(15) . . ?
O4 C6 C5 124.22(14) . . ?
C14 C13 N1 110.13(14) . . ?
C18 C13 N1 127.94(15) . . ?
C18 C13 C14 121.93(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.84(16) . . ?
C17 C16 H16 119.6 . . ?
C13 C18 H18 121.3 . . ?
C13 C18 C17 117.42(16) . . ?
C17 C18 H18 121.3 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.26(16) . . ?
C18 C17 H17 119.4 . . ?
C20 C25 H25 119.6 . . ?
C20 C25 C24 120.89(18) . . ?
C24 C25 H25 119.6 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.87(19) . . ?
C22 C21 H21 120.1 . . ?
O5 C7 C8 109.16(15) . . ?
O5 C7 C10 109.60(15) . . ?
O5 C7 C9 102.15(15) . . ?
C8 C7 C9 110.53(17) . . ?
C10 C7 C8 113.67(18) . . ?
C10 C7 C9 111.10(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.86(19) . . ?
C23 C24 H24 120.1 . . ?
O1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
O1 C2 C1 107.53(16) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C24 C23 H23 120.2 . . ?
C22 C23 C24 119.67(18) . . ?
C22 C23 H23 120.2 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C12 C11 C14 178.10(15) . . . . ?
O3 C12 C11 C4 -36.3(2) . . . . ?
O3 C12 C11 C5 29.3(2) . . . . ?
N1 C12 C11 C14 -2.63(16) . . . . ?
N1 C12 C11 C4 142.96(13) . . . . ?
N1 C12 C11 C5 -151.40(13) . . . . ?
N1 C13 C18 C17 -178.58(15) . . . . ?
C12 N1 C19 C20 109.98(17) . . . . ?
C12 N1 C13 C14 -0.79(17) . . . . ?
C12 N1 C13 C18 178.53(15) . . . . ?
C12 C11 C4 C5 106.23(15) . . . . ?
C12 C11 C4 C3 -2.8(2) . . . . ?
C12 C11 C5 C4 -105.71(15) . . . . ?
C12 C11 C5 C6 146.91(14) . . . . ?
C14 C11 C4 C5 -116.33(17) . . . . ?
C14 C11 C4 C3 134.60(16) . . . . ?
C14 C11 C5 C4 113.65(18) . . . . ?
C14 C11 C5 C6 6.3(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C20 C25 C24 C23 0.4(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C11 C14 C15 C16 179.34(16) . . . . ?
C11 C14 C13 N1 -0.96(16) . . . . ?
C11 C14 C13 C18 179.67(14) . . . . ?
C11 C4 C5 C6 108.48(16) . . . . ?
C11 C4 C3 O1 -72.91(18) . . . . ?
C11 C4 C3 O2 108.72(19) . . . . ?
C11 C5 C6 O5 -106.68(16) . . . . ?
C11 C5 C6 O4 73.1(2) . . . . ?
C4 C11 C5 C6 -107.38(16) . . . . ?
C4 C5 C6 O5 -176.23(13) . . . . ?
C4 C5 C6 O4 3.6(2) . . . . ?
C5 C11 C4 C3 -109.07(16) . . . . ?
C5 C4 C3 O1 -144.40(14) . . . . ?
C5 C4 C3 O2 37.2(2) . . . . ?
C15 C14 C11 C12 -177.39(16) . . . . ?
C15 C14 C11 C4 41.7(3) . . . . ?
C15 C14 C11 C5 -33.5(3) . . . . ?
C15 C14 C13 N1 178.67(13) . . . . ?
C15 C14 C13 C18 -0.7(2) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C3 O1 C2 C1 170.20(16) . . . . ?
C3 C4 C5 C11 109.72(16) . . . . ?
C3 C4 C5 C6 -141.80(15) . . . . ?
C19 N1 C12 O3 1.4(2) . . . . ?
C19 N1 C12 C11 -177.86(13) . . . . ?
C19 N1 C13 C14 179.22(13) . . . . ?
C19 N1 C13 C18 -1.5(2) . . . . ?
C19 C20 C25 C24 177.26(17) . . . . ?
C19 C20 C21 C22 -177.55(18) . . . . ?
C6 O5 C7 C8 63.1(2) . . . . ?
C6 O5 C7 C10 -62.0(2) . . . . ?
C6 O5 C7 C9 -179.83(16) . . . . ?
C13 N1 C12 O3 -178.57(15) . . . . ?
C13 N1 C12 C11 2.15(16) . . . . ?
C13 N1 C19 C20 -70.03(19) . . . . ?
C13 C14 C11 C12 2.17(15) . . . . ?
C13 C14 C11 C4 -138.76(15) . . . . ?
C13 C14 C11 C5 146.05(15) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C13 C18 C17 C16 0.2(3) . . . . ?
C25 C20 C19 N1 145.23(16) . . . . ?
C25 C20 C21 C22 0.3(3) . . . . ?
C25 C24 C23 C22 0.2(3) . . . . ?
C21 C20 C19 N1 -36.9(2) . . . . ?
C21 C20 C25 C24 -0.7(3) . . . . ?
C7 O5 C6 O4 0.5(2) . . . . ?
C7 O5 C6 C5 -179.70(13) . . . . ?
C24 C23 C22 C21 -0.5(4) . . . . ?
C2 O1 C3 O2 -5.1(2) . . . . ?
C2 O1 C3 C4 176.53(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
