# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2393609'
loop_
_audit_author_name
_audit_author_address
'Alex P. Andrews '
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2024-10-24 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        PYDB+TCNB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 B2 O4, C10 H2 N4 [+ solvent]'
_chemical_formula_sum            'C38 H34 B2 N4 O4'
_chemical_formula_weight         632.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7950(13)
_cell_length_b                   10.755(2)
_cell_length_c                   13.064(2)
_cell_angle_alpha                75.068(7)
_cell_angle_beta                 77.367(7)
_cell_angle_gamma                87.642(7)
_cell_volume                     900.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3331
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      20.78

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.167
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            24252
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3167
_reflns_number_gt                1908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Br uker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1148P)²+0.4755P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2345
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5508(5) 0.7954(3) 0.3674(2) 0.0437(7) Uani 1 1 d . . . . .
C2 C 0.5126(6) 0.6927(3) 0.4589(3) 0.0570(9) Uani 1 1 d . . . . .
H2 H 0.515349 0.609835 0.449272 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4711(5) 0.7070(3) 0.5626(2) 0.0539(9) Uani 1 1 d . . . . .
H3 H 0.446494 0.634581 0.620970 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4655(4) 0.8280(3) 0.5813(2) 0.0380(7) Uani 1 1 d . . . . .
C5 C 0.5033(4) 0.9372(2) 0.4912(2) 0.0322(6) Uani 1 1 d . . . . .
C6 C 0.5450(4) 0.9206(3) 0.3834(2) 0.0339(7) Uani 1 1 d . . . . .
C7 C 0.4234(5) 0.8482(3) 0.6874(2) 0.0442(8) Uani 1 1 d . . . . .
H7 H 0.398615 0.777096 0.746901 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4181(4) 0.9663(3) 0.7047(2) 0.0415(7) Uani 1 1 d . . . . .
H8 H 0.389714 0.974689 0.775485 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6669(6) 0.7775(3) 0.0735(3) 0.0586(9) Uani 1 1 d . . . . .
C10 C 0.6296(7) 0.6372(4) 0.1378(3) 0.0772(13) Uani 1 1 d . . . . .
C11 C 0.7656(12) 0.5407(5) 0.1036(4) 0.146(3) Uani 1 1 d . . . . .
H11A H 0.763030 0.541681 0.030207 0.219 Uiso 1 1 calc R U . . .
H11B H 0.900131 0.559270 0.107799 0.219 Uiso 1 1 calc R U . . .
H11C H 0.723429 0.457205 0.150220 0.219 Uiso 1 1 calc R U . . .
C12 C 0.4093(11) 0.5913(7) 0.1449(5) 0.148(3) Uani 1 1 d . . . . .
H12A H 0.395704 0.585524 0.074646 0.222 Uiso 1 1 calc R U . . .
H12B H 0.382915 0.508402 0.195448 0.222 Uiso 1 1 calc R U . . .
H12C H 0.314589 0.652043 0.168932 0.222 Uiso 1 1 calc R U . . .
C13 C 0.8867(8) 0.8113(6) 0.0253(4) 0.1080(17) Uani 1 1 d . . . . .
H13A H 0.935255 0.767849 -0.030763 0.162 Uiso 1 1 calc R U . . .
H13B H 0.901933 0.902604 -0.004906 0.162 Uiso 1 1 calc R U . . .
H13C H 0.962903 0.784966 0.080879 0.162 Uiso 1 1 calc R U . . .
C14 C 0.5452(8) 0.8247(5) -0.0118(3) 0.0931(15) Uani 1 1 d . . . . .
H14A H 0.584711 0.780290 -0.067859 0.140 Uiso 1 1 calc R U . . .
H14B H 0.404437 0.808648 0.020474 0.140 Uiso 1 1 calc R U . . .
H14C H 0.568596 0.915496 -0.042382 0.140 Uiso 1 1 calc R U . . .
C15 C 0.0746(5) 0.9368(4) 0.2984(3) 0.0666(10) Uani 1 1 d . . . . .
C16 C 0.0372(4) 0.9696(4) 0.4007(3) 0.0541(9) Uani 1 1 d . . . . .
C17 C -0.0004(5) 0.8724(4) 0.4954(3) 0.0577(9) Uani 1 1 d . . . . .
H17 H -0.001149 0.786882 0.492525 0.069 Uiso 1 1 calc R U . . .
C18 C -0.0371(4) 0.9025(3) 0.5949(3) 0.0534(9) Uani 1 1 d . . . . .
C19 C -0.0749(5) 0.7997(4) 0.6927(3) 0.0645(10) Uani 1 1 d . . . . .
B1 B 0.5956(6) 0.7630(3) 0.2548(3) 0.0477(9) Uani 1 1 d . . . . .
N1 N 0.1038(6) 0.9073(4) 0.2190(3) 0.0912(12) Uani 1 1 d . . . . .
N2 N -0.1037(6) 0.7172(4) 0.7685(3) 0.0896(11) Uani 1 1 d . . . . .
O1 O 0.6037(4) 0.8466(2) 0.15779(17) 0.0686(8) Uani 1 1 d . . . . .
O2 O 0.6258(5) 0.6410(2) 0.24731(18) 0.0786(9) Uani 1 1 d . . . . .


_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
C1 C2 1.387(4) . ?
C1 C6 1.413(4) . ?
C1 B1 1.561(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.418(4) . ?
C4 C7 1.423(4) . ?
C5 C5 1.424(5) 2_676 ?
C5 C6 1.431(4) . ?
C6 C8 1.429(4) 2_676 ?
C7 C8 1.344(4) . ?
C9 O1 1.462(4) . ?
C9 C14 1.504(5) . ?
C9 C13 1.508(6) . ?
C9 C10 1.526(5) . ?
C10 O2 1.437(4) . ?
C10 C11 1.453(6) . ?
C10 C12 1.572(7) . ?
C15 N1 1.137(4) . ?
C15 C16 1.436(5) . ?
C16 C17 1.381(5) . ?
C16 C18 1.392(5) 2_576 ?
C17 C18 1.387(5) . ?
C18 C19 1.440(5) . ?
C19 N2 1.133(5) . ?
B1 O1 1.344(4) . ?
B1 O2 1.344(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.6(3) . . ?
C2 C1 B1 117.1(3) . . ?
C6 C1 B1 125.3(3) . . ?
C3 C2 C1 123.4(3) . . ?
C2 C3 C4 120.6(3) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 C7 122.9(3) . . ?
C5 C4 C7 118.3(2) . . ?
C4 C5 C5 119.7(3) . 2_676 ?
C4 C5 C6 119.8(2) . . ?
C5 C5 C6 120.5(3) 2_676 . ?
C1 C6 C8 122.6(2) . 2_676 ?
C1 C6 C5 119.7(2) . . ?
C8 C6 C5 117.7(2) 2_676 . ?
C8 C7 C4 122.4(3) . . ?
C7 C8 C6 121.5(3) . 2_676 ?
O1 C9 C14 108.3(3) . . ?
O1 C9 C13 106.4(3) . . ?
C14 C9 C13 109.8(4) . . ?
O1 C9 C10 102.4(2) . . ?
C14 C9 C10 115.6(3) . . ?
C13 C9 C10 113.6(4) . . ?
O2 C10 C11 112.5(4) . . ?
O2 C10 C9 103.6(3) . . ?
C11 C10 C9 118.4(4) . . ?
O2 C10 C12 102.8(3) . . ?
C11 C10 C12 107.1(5) . . ?
C9 C10 C12 111.5(4) . . ?
N1 C15 C16 178.1(4) . . ?
C17 C16 C18 120.0(3) . 2_576 ?
C17 C16 C15 119.1(4) . . ?
C18 C16 C15 120.9(3) 2_576 . ?
C16 C17 C18 119.8(3) . . ?
C17 C18 C16 120.2(3) . 2_576 ?
C17 C18 C19 119.0(3) . . ?
C16 C18 C19 120.9(3) 2_576 . ?
N2 C19 C18 178.7(4) . . ?
O1 B1 O2 112.5(3) . . ?
O1 B1 C1 126.5(3) . . ?
O2 B1 C1 120.9(3) . . ?
B1 O1 C9 108.4(2) . . ?
B1 O2 C10 108.7(3) . . ?

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
C6 C1 C2 C3 -0.4(5) . . . . ?
B1 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C7 -179.9(3) . . . . ?
C3 C4 C5 C5 179.5(3) . . . 2_676 ?
C7 C4 C5 C5 -0.4(4) . . . 2_676 ?
C3 C4 C5 C6 0.3(4) . . . . ?
C7 C4 C5 C6 -179.6(2) . . . . ?
C2 C1 C6 C8 180.0(3) . . . 2_676 ?
B1 C1 C6 C8 -0.4(5) . . . 2_676 ?
C2 C1 C6 C5 0.8(4) . . . . ?
B1 C1 C6 C5 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C5 C5 C6 C1 -180.0(3) 2_676 . . . ?
C4 C5 C6 C8 180.0(2) . . . 2_676 ?
C5 C5 C6 C8 0.8(4) 2_676 . . 2_676 ?
C3 C4 C7 C8 -179.9(3) . . . . ?
C5 C4 C7 C8 0.1(4) . . . . ?
C4 C7 C8 C6 -0.1(4) . . . 2_676 ?
O1 C9 C10 O2 -20.7(4) . . . . ?
C14 C9 C10 O2 -138.2(3) . . . . ?
C13 C9 C10 O2 93.6(4) . . . . ?
O1 C9 C10 C11 -146.0(4) . . . . ?
C14 C9 C10 C11 96.5(5) . . . . ?
C13 C9 C10 C11 -31.7(5) . . . . ?
O1 C9 C10 C12 89.2(4) . . . . ?
C14 C9 C10 C12 -28.3(5) . . . . ?
C13 C9 C10 C12 -156.5(4) . . . . ?
C18 C16 C17 C18 -0.3(5) 2_576 . . . ?
C15 C16 C17 C18 -179.9(3) . . . . ?
C16 C17 C18 C16 0.4(5) . . . 2_576 ?
C16 C17 C18 C19 -179.7(3) . . . . ?
C2 C1 B1 O1 168.4(3) . . . . ?
C6 C1 B1 O1 -11.2(6) . . . . ?
C2 C1 B1 O2 -9.8(5) . . . . ?
C6 C1 B1 O2 170.6(3) . . . . ?
O2 B1 O1 C9 -6.5(4) . . . . ?
C1 B1 O1 C9 175.2(3) . . . . ?
C14 C9 O1 B1 139.6(3) . . . . ?
C13 C9 O1 B1 -102.5(4) . . . . ?
C10 C9 O1 B1 17.0(4) . . . . ?
O1 B1 O2 C10 -8.0(4) . . . . ?
C1 B1 O2 C10 170.5(3) . . . . ?
C11 C10 O2 B1 147.1(4) . . . . ?
C9 C10 O2 B1 18.1(4) . . . . ?
C12 C10 O2 B1 -98.1(4) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.059



_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_b5pyb
_database_code_depnum_ccdc_archive 'CCDC 2393610'
loop_
_audit_author_name
_audit_author_address
'Alex P. Andrews '
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2024-10-24 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        PYDB
_chemical_formula_moiety         'C28 H32 B2 O4'
_chemical_formula_sum            'C28 H32 B2 O4'
_chemical_formula_weight         454.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5742(7)
_cell_length_b                   10.9869(8)
_cell_length_c                   11.2991(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.084(2)
_cell_angle_gamma                90
_cell_volume                     1283.62(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6352
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_min         2.400
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2350
_reflns_number_total             3206
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.062
_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)+(0.1270P)²+0.3804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2197
_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 Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A)
2.b Idealised Me refined as rotating group:
 C00E(H00B,H00C,H00D), C00F(H00E,H00F,H00G), C00G(H00H,H00I,H00J), C00H(H00K,
 H00L,H00M)
;
_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
O001 O 0.41898(13) 0.41949(13) 0.65995(14) 0.0555(4) Uani 1 1 d . . . . .
O002 O 0.21161(13) 0.41860(13) 0.55504(14) 0.0550(4) Uani 1 1 d . . . . .
C003 C 0.44687(14) 0.04130(13) 0.48470(13) 0.0286(3) Uani 1 1 d . . . . .
C004 C 0.44788(14) 0.15400(13) 0.54723(13) 0.0297(4) Uani 1 1 d . . . . .
C005 C 0.33968(14) 0.01042(14) 0.39173(14) 0.0324(4) Uani 1 1 d . . . . .
C006 C 0.34075(15) 0.23401(15) 0.51780(14) 0.0336(4) Uani 1 1 d . . . . .
C007 C 0.55882(16) 0.18106(15) 0.64057(15) 0.0372(4) Uani 1 1 d . . . . .
H007 H 0.561684 0.254391 0.682152 0.045 Uiso 1 1 calc R U . . .
C008 C 0.23628(16) 0.19899(16) 0.42640(15) 0.0379(4) Uani 1 1 d . . . . .
H008 H 0.164914 0.250230 0.407132 0.045 Uiso 1 1 calc R U . . .
C009 C 0.65898(16) 0.10317(16) 0.66967(16) 0.0395(4) Uani 1 1 d . . . . .
H009 H 0.728862 0.123818 0.731138 0.047 Uiso 1 1 calc R U . . .
C00A C 0.23552(16) 0.09115(16) 0.36396(15) 0.0388(4) Uani 1 1 d . . . . .
H00A H 0.164938 0.071890 0.302674 0.047 Uiso 1 1 calc R U . . .
C00B C 0.3557(2) 0.52241(19) 0.7054(2) 0.0583(6) Uani 1 1 d . . . . .
C00C C 0.2324(2) 0.5394(2) 0.6074(2) 0.0579(6) Uani 1 1 d . . . . .
B00D B 0.32696(19) 0.35848(18) 0.58035(18) 0.0379(4) Uani 1 1 d . . . . .
C00E C 0.1151(3) 0.5823(3) 0.6483(3) 0.0898(10) Uani 1 1 d . . . . .
H00B H 0.046288 0.595179 0.579144 0.135 Uiso 1 1 calc R U . . .
H00C H 0.134049 0.657223 0.692046 0.135 Uiso 1 1 calc R U . . .
H00D H 0.089201 0.522015 0.700007 0.135 Uiso 1 1 calc R U . . .
C00F C 0.3251(4) 0.4761(4) 0.8244(3) 0.1124(14) Uani 1 1 d . . . . .
H00E H 0.273939 0.403384 0.809137 0.169 Uiso 1 1 calc R U . . .
H00F H 0.277883 0.537309 0.857639 0.169 Uiso 1 1 calc R U . . .
H00G H 0.404346 0.458623 0.880765 0.169 Uiso 1 1 calc R U . . .
C00G C 0.4451(3) 0.6287(3) 0.7297(4) 0.1237(17) Uani 1 1 d . . . . .
H00H H 0.517997 0.608293 0.792699 0.186 Uiso 1 1 calc R U . . .
H00I H 0.400315 0.696938 0.754734 0.186 Uiso 1 1 calc R U . . .
H00J H 0.474431 0.649355 0.657412 0.186 Uiso 1 1 calc R U . . .
C00H C 0.2566(5) 0.6200(3) 0.5037(3) 0.1135(14) Uani 1 1 d . . . . .
H00K H 0.333102 0.592708 0.478426 0.170 Uiso 1 1 calc R U . . .
H00L H 0.268038 0.702817 0.530804 0.170 Uiso 1 1 calc R U . . .
H00M H 0.183931 0.614824 0.436834 0.170 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
O001 C00B 1.461(2) . ?
O001 B00D 1.356(2) . ?
O002 C00C 1.451(2) . ?
O002 B00D 1.364(2) . ?
C003 C003 1.429(3) 3_656 ?
C003 C004 1.425(2) . ?
C003 C005 1.416(2) . ?
C004 C006 1.417(2) . ?
C004 C007 1.435(2) . ?
C005 C009 1.429(2) 3_656 ?
C005 C00A 1.398(2) . ?
C006 C008 1.399(2) . ?
C006 B00D 1.560(2) . ?
C007 H007 0.9300 . ?
C007 C009 1.348(2) . ?
C008 H008 0.9300 . ?
C008 C00A 1.378(2) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00B C00C 1.535(3) . ?
C00B C00F 1.534(4) . ?
C00B C00G 1.491(4) . ?
C00C C00E 1.488(3) . ?
C00C C00H 1.532(4) . ?
C00E H00B 0.9600 . ?
C00E H00C 0.9600 . ?
C00E H00D 0.9600 . ?
C00F H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00H H00L 0.9600 . ?
C00H H00M 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B00D O001 C00B 107.33(15) . . ?
B00D O002 C00C 107.76(15) . . ?
C004 C003 C003 120.53(16) . 3_656 ?
C005 C003 C003 119.60(17) . 3_656 ?
C005 C003 C004 119.87(13) . . ?
C003 C004 C007 117.70(13) . . ?
C006 C004 C003 120.00(13) . . ?
C006 C004 C007 122.29(14) . . ?
C003 C005 C009 118.79(14) . 3_656 ?
C00A C005 C003 119.03(14) . . ?
C00A C005 C009 122.18(14) . 3_656 ?
C004 C006 B00D 125.68(14) . . ?
C008 C006 C004 118.13(15) . . ?
C008 C006 B00D 116.18(14) . . ?
C004 C007 H007 119.1 . . ?
C009 C007 C004 121.85(15) . . ?
C009 C007 H007 119.1 . . ?
C006 C008 H008 118.9 . . ?
C00A C008 C006 122.23(15) . . ?
C00A C008 H008 118.9 . . ?
C005 C009 H009 119.2 3_656 . ?
C007 C009 C005 121.54(15) . 3_656 ?
C007 C009 H009 119.2 . . ?
C005 C00A H00A 119.6 . . ?
C008 C00A C005 120.72(15) . . ?
C008 C00A H00A 119.6 . . ?
O001 C00B C00C 102.91(16) . . ?
O001 C00B C00F 104.3(2) . . ?
O001 C00B C00G 110.6(2) . . ?
C00F C00B C00C 111.7(2) . . ?
C00G C00B C00C 116.6(2) . . ?
C00G C00B C00F 109.9(3) . . ?
O002 C00C C00B 102.47(15) . . ?
O002 C00C C00E 110.5(2) . . ?
O002 C00C C00H 104.6(2) . . ?
C00E C00C C00B 116.9(2) . . ?
C00E C00C C00H 109.8(3) . . ?
C00H C00C C00B 111.7(3) . . ?
O001 B00D O002 112.69(15) . . ?
O001 B00D C006 127.71(16) . . ?
O002 B00D C006 119.60(16) . . ?
C00C C00E H00B 109.5 . . ?
C00C C00E H00C 109.5 . . ?
C00C C00E H00D 109.5 . . ?
H00B C00E H00C 109.5 . . ?
H00B C00E H00D 109.5 . . ?
H00C C00E H00D 109.5 . . ?
C00B C00F H00E 109.5 . . ?
C00B C00F H00F 109.5 . . ?
C00B C00F H00G 109.5 . . ?
H00E C00F H00F 109.5 . . ?
H00E C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00B C00G H00H 109.5 . . ?
C00B C00G H00I 109.5 . . ?
C00B C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 109.5 . . ?
C00C C00H H00K 109.5 . . ?
C00C C00H H00L 109.5 . . ?
C00C C00H H00M 109.5 . . ?
H00K C00H H00L 109.5 . . ?
H00K C00H H00M 109.5 . . ?
H00L C00H H00M 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
O001 C00B C00C O002 25.6(2) . . . . ?
O001 C00B C00C C00E 146.6(2) . . . . ?
O001 C00B C00C C00H -85.8(2) . . . . ?
C003 C003 C004 C006 -178.68(17) 3_656 . . . ?
C003 C003 C004 C007 0.3(3) 3_656 . . . ?
C003 C003 C005 C009 -0.2(3) 3_656 . . 3_656 ?
C003 C003 C005 C00A 179.02(17) 3_656 . . . ?
C003 C004 C006 C008 -0.3(2) . . . . ?
C003 C004 C006 B00D 178.51(15) . . . . ?
C003 C004 C007 C009 -0.4(3) . . . . ?
C003 C005 C00A C008 -0.4(3) . . . . ?
C004 C003 C005 C009 179.98(15) . . . 3_656 ?
C004 C003 C005 C00A -0.8(2) . . . . ?
C004 C006 C008 C00A -0.9(3) . . . . ?
C004 C006 B00D O001 9.9(3) . . . . ?
C004 C006 B00D O002 -170.88(16) . . . . ?
C004 C007 C009 C005 0.5(3) . . . 3_656 ?
C005 C003 C004 C006 1.1(2) . . . . ?
C005 C003 C004 C007 -179.93(14) . . . . ?
C006 C004 C007 C009 178.53(16) . . . . ?
C006 C008 C00A C005 1.3(3) . . . . ?
C007 C004 C006 C008 -179.20(15) . . . . ?
C007 C004 C006 B00D -0.4(3) . . . . ?
C008 C006 B00D O001 -171.31(19) . . . . ?
C008 C006 B00D O002 7.9(2) . . . . ?
C009 C005 C00A C008 178.82(17) 3_656 . . . ?
C00B O001 B00D O002 8.3(2) . . . . ?
C00B O001 B00D C006 -172.46(19) . . . . ?
C00C O002 B00D O001 9.4(2) . . . . ?
C00C O002 B00D C006 -169.91(17) . . . . ?
B00D O001 C00B C00C -21.1(2) . . . . ?
B00D O001 C00B C00F 95.6(2) . . . . ?
B00D O001 C00B C00G -146.3(3) . . . . ?
B00D O002 C00C C00B -21.8(2) . . . . ?
B00D O002 C00C C00E -147.1(2) . . . . ?
B00D O002 C00C C00H 94.9(2) . . . . ?
B00D C006 C008 C00A -179.82(16) . . . . ?
C00F C00B C00C O002 -85.7(2) . . . . ?
C00F C00B C00C C00E 35.3(3) . . . . ?
C00F C00B C00C C00H 162.9(2) . . . . ?
C00G C00B C00C O002 146.8(2) . . . . ?
C00G C00B C00C C00E -92.2(3) . . . . ?
C00G C00B C00C C00H 35.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
