# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cu_1109_5_0m
_database_code_depnum_ccdc_archive 'CCDC 2071524'
loop_
_audit_author_name
_audit_author_address
'Haodong Sun'
;NorthwesternPolytechnicalUniversity
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2020-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17
_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'
B B 0.0090 0.0039 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6701(3)
_cell_length_b                   9.2394(3)
_cell_length_c                   21.0354(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.4810(10)
_cell_angle_gamma                90
_cell_volume                     1651.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      5.21
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.1738
_exptl_absorpt_correction_T_min  0.0661
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.3803.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18436
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         5.206
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_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           1.0
_diffrn_source_power             0.05
_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                3135
_reflns_number_total             3336
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.036
_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)+(0.0520P)²+0.4005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1019
_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:
 C2(H2), C11(H11), C12(H12), C9(H9), C6(H6), C3(H3), C10(H10), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C)
;
_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
O2 O 0.69903(9) 0.72387(8) 0.31639(4) 0.03492(19) Uani 1 1 d . . . . .
O3 O 0.61127(10) 0.48978(9) 0.30778(4) 0.0376(2) Uani 1 1 d . . . . .
O1 O 0.86474(9) 0.61459(9) 0.44409(4) 0.0395(2) Uani 1 1 d . . . . .
C13 C 0.53779(13) 0.63887(12) 0.40085(5) 0.0335(2) Uani 1 1 d . . . . .
C1 C 0.88038(13) 0.78787(12) 0.52728(5) 0.0340(2) Uani 1 1 d . . . . .
C8 C 0.61705(13) 0.68790(12) 0.46189(5) 0.0338(2) Uani 1 1 d . . . . .
C7 C 0.79241(13) 0.69248(12) 0.47504(5) 0.0337(2) Uani 1 1 d . . . . .
C2 C 1.01888(13) 0.73525(13) 0.56544(5) 0.0363(3) Uani 1 1 d . . . . .
H2 H 1.050984 0.638401 0.560220 0.044 Uiso 1 1 calc R U . . .
C17 C 0.76901(13) 0.65807(12) 0.26554(5) 0.0342(2) Uani 1 1 d . . . . .
C11 C 0.29538(14) 0.63548(14) 0.44235(6) 0.0408(3) Uani 1 1 d . . . . .
H11 H 0.185596 0.616692 0.435610 0.049 Uiso 1 1 calc R U . . .
C12 C 0.37636(14) 0.61336(13) 0.39244(6) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.320462 0.580034 0.351585 0.045 Uiso 1 1 calc R U . . .
C9 C 0.53566(14) 0.71188(14) 0.51173(6) 0.0395(3) Uani 1 1 d . . . . .
H9 H 0.590144 0.746733 0.552541 0.047 Uiso 1 1 calc R U . . .
C19 C 0.76372(15) 0.76743(14) 0.21136(6) 0.0423(3) Uani 1 1 d . . . . .
H19A H 0.655608 0.802269 0.197067 0.063 Uiso 1 1 calc R U . . .
H19B H 0.799358 0.721485 0.174839 0.063 Uiso 1 1 calc R U . . .
H19C H 0.832770 0.849185 0.227175 0.063 Uiso 1 1 calc R U . . .
C6 C 0.83365(14) 0.93000(13) 0.53543(6) 0.0385(3) Uani 1 1 d . . . . .
H6 H 0.737430 0.965365 0.510573 0.046 Uiso 1 1 calc R U . . .
C14 C 0.66305(14) 0.52216(13) 0.24709(5) 0.0359(3) Uani 1 1 d . . . . .
C18 C 0.93874(14) 0.62089(14) 0.29597(6) 0.0416(3) Uani 1 1 d . . . . .
H18A H 0.992913 0.708016 0.315484 0.062 Uiso 1 1 calc R U . . .
H18B H 0.992272 0.583665 0.262473 0.062 Uiso 1 1 calc R U . . .
H18C H 0.940268 0.547058 0.329537 0.062 Uiso 1 1 calc R U . . .
C3 C 1.10991(14) 0.82460(15) 0.61113(6) 0.0414(3) Uani 1 1 d . . . . .
H3 H 1.202937 0.787940 0.637957 0.050 Uiso 1 1 calc R U . . .
C10 C 0.37543(15) 0.68502(15) 0.50192(6) 0.0434(3) Uani 1 1 d . . . . .
H10 H 0.320452 0.700636 0.536135 0.052 Uiso 1 1 calc R U . . .
C16 C 0.74713(17) 0.39038(14) 0.22802(7) 0.0464(3) Uani 1 1 d . . . . .
H16A H 0.832803 0.363214 0.263863 0.070 Uiso 1 1 calc R U . . .
H16B H 0.790441 0.412757 0.189525 0.070 Uiso 1 1 calc R U . . .
H16C H 0.672574 0.309866 0.218311 0.070 Uiso 1 1 calc R U . . .
C5 C 0.92773(16) 1.01945(14) 0.57982(6) 0.0433(3) Uani 1 1 d . . . . .
H5 H 0.897624 1.117206 0.584280 0.052 Uiso 1 1 calc R U . . .
C4 C 1.06571(15) 0.96703(15) 0.61779(6) 0.0440(3) Uani 1 1 d . . . . .
H4 H 1.129773 1.028648 0.648294 0.053 Uiso 1 1 calc R U . . .
C15 C 0.51513(16) 0.55350(16) 0.19670(6) 0.0479(3) Uani 1 1 d . . . . .
H15A H 0.442449 0.471544 0.194299 0.072 Uiso 1 1 calc R U . . .
H15B H 0.543203 0.568132 0.154275 0.072 Uiso 1 1 calc R U . . .
H15C H 0.464397 0.641029 0.209043 0.072 Uiso 1 1 calc R U . . .
B1 B 0.62393(15) 0.61563(14) 0.34254(6) 0.0337(3) 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
O2 C17 1.4630(13) . ?
O2 B1 1.3673(15) . ?
O3 C14 1.4660(13) . ?
O3 B1 1.3663(15) . ?
O1 C7 1.2237(13) . ?
C13 C8 1.4053(16) . ?
C13 C12 1.3954(16) . ?
C13 B1 1.5726(16) . ?
C1 C7 1.4941(16) . ?
C1 C2 1.3925(16) . ?
C1 C6 1.3949(16) . ?
C8 C7 1.4908(15) . ?
C8 C9 1.3931(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3878(17) . ?
C17 C19 1.5169(16) . ?
C17 C14 1.5587(16) . ?
C17 C18 1.5226(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3893(17) . ?
C11 C10 1.3840(18) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.3856(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C5 1.3845(18) . ?
C14 C16 1.5137(17) . ?
C14 C15 1.5202(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.3855(19) . ?
C10 H10 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.3868(19) . ?
C4 H4 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
B1 O2 C17 106.87(9) . . ?
B1 O3 C14 106.65(9) . . ?
C8 C13 B1 122.34(10) . . ?
C12 C13 C8 117.78(10) . . ?
C12 C13 B1 119.88(10) . . ?
C2 C1 C7 118.26(10) . . ?
C2 C1 C6 119.74(11) . . ?
C6 C1 C7 121.84(10) . . ?
C13 C8 C7 118.28(10) . . ?
C9 C8 C13 120.66(10) . . ?
C9 C8 C7 120.44(10) . . ?
O1 C7 C1 119.83(10) . . ?
O1 C7 C8 119.76(10) . . ?
C8 C7 C1 120.38(9) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.86(11) . . ?
C3 C2 H2 120.1 . . ?
O2 C17 C19 108.52(9) . . ?
O2 C17 C14 101.96(8) . . ?
O2 C17 C18 107.04(9) . . ?
C19 C17 C14 114.93(9) . . ?
C19 C17 C18 110.38(10) . . ?
C18 C17 C14 113.28(10) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.67(11) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.62(11) . . ?
C11 C12 H12 119.2 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.17(11) . . ?
C10 C9 H9 119.9 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.89(11) . . ?
C5 C6 H6 120.1 . . ?
O3 C14 C17 102.42(8) . . ?
O3 C14 C16 108.29(9) . . ?
O3 C14 C15 106.50(9) . . ?
C16 C14 C17 115.02(10) . . ?
C16 C14 C15 110.63(10) . . ?
C15 C14 C17 113.18(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.29(11) . . ?
C4 C3 H3 119.9 . . ?
C11 C10 C9 120.08(11) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.32(12) . . ?
C4 C5 H5 119.8 . . ?
C3 C4 C5 119.85(11) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 B1 C13 123.51(10) . . ?
O3 B1 O2 113.65(10) . . ?
O3 B1 C13 122.25(10) . . ?

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 C17 C14 O3 -28.46(10) . . . . ?
O2 C17 C14 C16 -145.68(10) . . . . ?
O2 C17 C14 C15 85.79(11) . . . . ?
C13 C8 C7 O1 -23.39(16) . . . . ?
C13 C8 C7 C1 158.68(10) . . . . ?
C13 C8 C9 C10 1.16(18) . . . . ?
C1 C2 C3 C4 -1.66(18) . . . . ?
C1 C6 C5 C4 -2.16(18) . . . . ?
C8 C13 C12 C11 0.09(17) . . . . ?
C8 C13 B1 O2 -60.32(16) . . . . ?
C8 C13 B1 O3 129.08(12) . . . . ?
C8 C9 C10 C11 -0.58(19) . . . . ?
C7 C1 C2 C3 175.15(10) . . . . ?
C7 C1 C6 C5 -173.08(11) . . . . ?
C7 C8 C9 C10 -169.69(11) . . . . ?
C2 C1 C7 O1 -37.21(16) . . . . ?
C2 C1 C7 C8 140.72(11) . . . . ?
C2 C1 C6 C5 2.19(17) . . . . ?
C2 C3 C4 C5 1.70(18) . . . . ?
C17 O2 B1 O3 -10.98(12) . . . . ?
C17 O2 B1 C13 177.69(10) . . . . ?
C12 C13 C8 C7 170.14(10) . . . . ?
C12 C13 C8 C9 -0.90(17) . . . . ?
C12 C13 B1 O2 118.37(13) . . . . ?
C12 C13 B1 O3 -52.23(16) . . . . ?
C12 C11 C10 C9 -0.23(19) . . . . ?
C9 C8 C7 O1 147.67(12) . . . . ?
C9 C8 C7 C1 -30.26(16) . . . . ?
C19 C17 C14 O3 -145.61(10) . . . . ?
C19 C17 C14 C16 97.17(12) . . . . ?
C19 C17 C14 C15 -31.36(14) . . . . ?
C6 C1 C7 O1 138.13(12) . . . . ?
C6 C1 C7 C8 -43.94(15) . . . . ?
C6 C1 C2 C3 -0.29(17) . . . . ?
C6 C5 C4 C3 0.21(19) . . . . ?
C14 O3 B1 O2 -8.71(13) . . . . ?
C14 O3 B1 C13 162.74(10) . . . . ?
C18 C17 C14 O3 86.21(11) . . . . ?
C18 C17 C14 C16 -31.02(14) . . . . ?
C18 C17 C14 C15 -159.54(10) . . . . ?
C10 C11 C12 C13 0.47(18) . . . . ?
B1 O2 C17 C19 145.94(10) . . . . ?
B1 O2 C17 C14 24.26(11) . . . . ?
B1 O2 C17 C18 -94.92(10) . . . . ?
B1 O3 C14 C17 23.03(11) . . . . ?
B1 O3 C14 C16 144.96(10) . . . . ?
B1 O3 C14 C15 -96.03(11) . . . . ?
B1 C13 C8 C7 -11.15(16) . . . . ?
B1 C13 C8 C9 177.81(11) . . . . ?
B1 C13 C12 C11 -178.65(10) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.467 0.000 0.556 7.1 0.0 ?
2 0.467 0.500 0.056 7.1 0.0 ?
3 0.533 0.000 0.444 7.1 0.0 ?
4 0.533 0.500 0.944 7.1 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_cu_1125_5_0m
_database_code_depnum_ccdc_archive 'CCDC 2071525'
loop_
_audit_author_name
_audit_author_address
'Haodong Sun'
;NorthwesternPolytechnicalUniversity
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.043(C19 H21 B O3)'
_chemical_formula_sum            'C0.82 H0.90 B0.04 O0.13'
_chemical_formula_weight         13.25
_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'
B B 0.0090 0.0039 '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      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                   6.20100(10)
_cell_length_b                   10.5943(2)
_cell_length_c                   25.4359(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.0660(10)
_cell_angle_gamma                90
_cell_volume                     1669.93(5)
_cell_formula_units_Z            93
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.52
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0117
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.1342.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23621
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.522
_diffrn_reflns_theta_min         3.477
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_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           1.0
_diffrn_source_power             0.05
_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                3043
_reflns_number_total             3399
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052
_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     212
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.058
_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)+(0.1182P)²+0.1501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1680
_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:
 C5(H5), C13(H13), C4(H4), C12(H12), C10(H10), C9(H9), C3(H3), C2(H2), C1(H1)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C)
;
_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
O3 O 0.38920(16) 0.13016(9) 0.30328(4) 0.0546(3) Uani 1 1 d . . . . .
O2 O 0.66273(16) 0.01393(9) 0.34196(4) 0.0554(3) Uani 1 1 d . . . . .
O1 O 1.14165(17) 0.61269(11) 0.42010(5) 0.0674(3) Uani 1 1 d . . . . .
C5 C 0.6207(2) 0.64446(13) 0.47727(5) 0.0517(3) Uani 1 1 d . . . . .
H5 H 0.563460 0.563296 0.469158 0.062 Uiso 1 1 calc R U . . .
C13 C 0.6426(2) 0.47637(13) 0.37817(5) 0.0500(3) Uani 1 1 d . . . . .
H13 H 0.559118 0.551560 0.377396 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5072(2) 0.72546(14) 0.50893(6) 0.0545(3) Uani 1 1 d . . . . .
H4 H 0.373728 0.699451 0.522582 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5602(2) 0.36660(13) 0.35561(5) 0.0497(3) Uani 1 1 d . . . . .
H12 H 0.420941 0.368136 0.338767 0.060 Uiso 1 1 calc R U . . .
C11 C 0.6769(2) 0.25378(13) 0.35706(5) 0.0493(3) Uani 1 1 d . . . . .
C7 C 0.9506(2) 0.59254(14) 0.42571(6) 0.0525(3) Uani 1 1 d . . . . .
C8 C 0.8493(2) 0.47598(13) 0.40209(5) 0.0490(3) Uani 1 1 d . . . . .
C6 C 0.8174(2) 0.68042(13) 0.45717(5) 0.0511(3) Uani 1 1 d . . . . .
C10 C 0.8840(2) 0.25499(13) 0.38119(5) 0.0512(3) Uani 1 1 d . . . . .
H10 H 0.966383 0.179387 0.382739 0.061 Uiso 1 1 calc R U . . .
C9 C 0.9701(2) 0.36468(13) 0.40276(6) 0.0510(3) Uani 1 1 d . . . . .
H9 H 1.112022 0.364273 0.418109 0.061 Uiso 1 1 calc R U . . .
C17 C 0.4675(3) 0.00724(17) 0.22741(7) 0.0660(4) Uani 1 1 d . . . . .
H17A H 0.390629 0.069512 0.205270 0.099 Uiso 1 1 calc R U . . .
H17B H 0.455892 -0.076142 0.210871 0.099 Uiso 1 1 calc R U . . .
H17C H 0.619928 0.031135 0.231413 0.099 Uiso 1 1 calc R U . . .
C3 C 0.5881(3) 0.84373(15) 0.52061(7) 0.0608(4) Uani 1 1 d . . . . .
H3 H 0.510794 0.899406 0.542337 0.073 Uiso 1 1 calc R U . . .
C18 C 0.1312(2) -0.03188(17) 0.27615(7) 0.0633(4) Uani 1 1 d . . . . .
H18A H 0.063129 -0.017581 0.309813 0.095 Uiso 1 1 calc R U . . .
H18B H 0.117186 -0.121063 0.266387 0.095 Uiso 1 1 calc R U . . .
H18C H 0.060165 0.020514 0.248909 0.095 Uiso 1 1 calc R U . . .
C15 C 0.3683(2) 0.00293(13) 0.28133(6) 0.0529(3) Uani 1 1 d . . . . .
C2 C 0.7829(3) 0.88107(16) 0.50049(8) 0.0714(5) Uani 1 1 d . . . . .
H2 H 0.838021 0.962879 0.508285 0.086 Uiso 1 1 calc R U . . .
B1 B 0.5756(3) 0.13037(15) 0.33363(6) 0.0504(4) Uani 1 1 d . . . . .
C1 C 0.8978(3) 0.80036(16) 0.46917(7) 0.0632(4) Uani 1 1 d . . . . .
H1 H 1.031657 0.826688 0.455813 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5016(2) -0.07737(14) 0.32215(6) 0.0558(4) Uani 1 1 d . . . . .
C19 C 0.3733(3) -0.11774(17) 0.36914(7) 0.0698(4) Uani 1 1 d . . . . .
H19A H 0.471883 -0.151320 0.396686 0.105 Uiso 1 1 calc R U . . .
H19B H 0.269283 -0.183151 0.358213 0.105 Uiso 1 1 calc R U . . .
H19C H 0.295977 -0.044760 0.382813 0.105 Uiso 1 1 calc R U . . .
C16 C 0.6176(3) -0.19012(16) 0.29959(8) 0.0702(5) Uani 1 1 d . . . . .
H16A H 0.713488 -0.161507 0.272201 0.105 Uiso 1 1 calc R U . . .
H16B H 0.511435 -0.249441 0.284348 0.105 Uiso 1 1 calc R U . . .
H16C H 0.702852 -0.232202 0.327648 0.105 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
O3 C15 1.4630(17) . ?
O3 B1 1.3664(19) . ?
O2 B1 1.3604(19) . ?
O2 C14 1.4669(17) . ?
O1 C7 1.2172(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(2) . ?
C5 C6 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.3864(19) . ?
C13 C8 1.3987(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.378(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.3972(19) . ?
C11 C10 1.4034(19) . ?
C11 B1 1.560(2) . ?
C7 C8 1.5011(19) . ?
C7 C6 1.496(2) . ?
C8 C9 1.3965(19) . ?
C6 C1 1.395(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.3839(19) . ?
C9 H9 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C15 1.524(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C15 1.517(2) . ?
C15 C14 1.556(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(2) . ?
C1 H1 0.9500 . ?
C14 C19 1.521(2) . ?
C14 C16 1.518(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
B1 O3 C15 106.18(11) . . ?
B1 O2 C14 106.41(11) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.91(13) . . ?
C6 C5 H5 119.5 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C8 119.74(13) . . ?
C8 C13 H13 120.1 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.98(14) . . ?
C3 C4 H4 120.0 . . ?
C13 C12 H12 119.2 . . ?
C13 C12 C11 121.57(12) . . ?
C11 C12 H12 119.2 . . ?
C12 C11 C10 117.96(12) . . ?
C12 C11 B1 120.38(12) . . ?
C10 C11 B1 121.64(13) . . ?
O1 C7 C8 119.49(13) . . ?
O1 C7 C6 120.80(13) . . ?
C6 C7 C8 119.68(12) . . ?
C13 C8 C7 122.36(12) . . ?
C9 C8 C13 119.36(12) . . ?
C9 C8 C7 118.25(12) . . ?
C5 C6 C7 122.27(12) . . ?
C5 C6 C1 118.67(13) . . ?
C1 C6 C7 118.97(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.98(13) . . ?
C9 C10 H10 119.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.35(12) . . ?
C10 C9 H9 119.8 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.68(14) . . ?
C2 C3 H3 120.2 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
O3 C15 C17 106.43(12) . . ?
O3 C15 C18 109.23(12) . . ?
O3 C15 C14 102.20(11) . . ?
C17 C15 C14 113.25(13) . . ?
C18 C15 C17 110.53(13) . . ?
C18 C15 C14 114.50(13) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.65(15) . . ?
C1 C2 H2 119.7 . . ?
O3 B1 C11 122.56(13) . . ?
O2 B1 O3 114.19(12) . . ?
O2 B1 C11 123.25(13) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 C6 120.11(14) . . ?
C2 C1 H1 119.9 . . ?
O2 C14 C15 101.98(11) . . ?
O2 C14 C19 106.53(12) . . ?
O2 C14 C16 108.81(12) . . ?
C19 C14 C15 113.44(13) . . ?
C16 C14 C15 115.18(14) . . ?
C16 C14 C19 110.14(14) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O3 C15 C14 O2 -29.48(13) . . . . ?
O3 C15 C14 C19 84.67(14) . . . . ?
O3 C15 C14 C16 -147.12(12) . . . . ?
O1 C7 C8 C13 -140.27(15) . . . . ?
O1 C7 C8 C9 37.6(2) . . . . ?
O1 C7 C6 C5 -161.00(15) . . . . ?
O1 C7 C6 C1 15.6(2) . . . . ?
C5 C4 C3 C2 0.1(2) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C13 C12 C11 C10 -1.4(2) . . . . ?
C13 C12 C11 B1 177.15(12) . . . . ?
C13 C8 C9 C10 -1.7(2) . . . . ?
C4 C5 C6 C7 176.07(13) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C12 C13 C8 C7 178.04(12) . . . . ?
C12 C13 C8 C9 0.2(2) . . . . ?
C12 C11 C10 C9 -0.2(2) . . . . ?
C12 C11 B1 O3 11.5(2) . . . . ?
C12 C11 B1 O2 -167.80(13) . . . . ?
C11 C10 C9 C8 1.7(2) . . . . ?
C7 C8 C9 C10 -179.64(12) . . . . ?
C7 C6 C1 C2 -176.66(16) . . . . ?
C8 C13 C12 C11 1.4(2) . . . . ?
C8 C7 C6 C5 17.1(2) . . . . ?
C8 C7 C6 C1 -166.26(13) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C6 C7 C8 C13 41.56(19) . . . . ?
C6 C7 C8 C9 -140.53(14) . . . . ?
C10 C11 B1 O3 -170.07(13) . . . . ?
C10 C11 B1 O2 10.7(2) . . . . ?
C17 C15 C14 O2 84.59(14) . . . . ?
C17 C15 C14 C19 -161.26(13) . . . . ?
C17 C15 C14 C16 -33.05(17) . . . . ?
C3 C2 C1 C6 0.5(3) . . . . ?
C18 C15 C14 O2 -147.44(12) . . . . ?
C18 C15 C14 C19 -33.29(18) . . . . ?
C18 C15 C14 C16 94.92(16) . . . . ?
C15 O3 B1 O2 -10.66(16) . . . . ?
C15 O3 B1 C11 170.01(12) . . . . ?
B1 O3 C15 C17 -94.28(14) . . . . ?
B1 O3 C15 C18 146.37(13) . . . . ?
B1 O3 C15 C14 24.72(14) . . . . ?
B1 O2 C14 C15 24.11(14) . . . . ?
B1 O2 C14 C19 -95.05(14) . . . . ?
B1 O2 C14 C16 146.23(14) . . . . ?
B1 C11 C10 C9 -178.66(13) . . . . ?
C14 O2 B1 O3 -9.64(16) . . . . ?
C14 O2 B1 C11 169.68(13) . . . . ?

_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_cu_0108_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2071526'
loop_
_audit_author_name
_audit_author_address
'Haodong Sun'
;NorthwesternPolytechnicalUniversity
China
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_audit_creation_date             2021-01-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        c-BP4Bpin
_chemical_formula_moiety         'C19 H21 B O3'
_chemical_formula_sum            'C19 H21 B O3'
_chemical_formula_weight         308.17
_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'
B B 0.0090 0.0039 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3412(3)
_cell_length_b                   11.8434(3)
_cell_length_c                   12.7459(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.491(2)
_cell_angle_gamma                90
_cell_volume                     1721.27(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4856
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      74.51
_cell_measurement_theta_min      3.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0116
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            15000
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.701
_diffrn_reflns_theta_min         3.877
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_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           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2771
_reflns_number_total             3496
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.081
_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)+(0.1297P)²+0.0836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1957
_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:
 C10(H10), C13(H13), C12(H12), C4(H4), C9(H9), C3(H3), C6(H6), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_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
O3 O 0.50097(11) 0.15877(12) 0.57762(11) 0.0678(4) Uani 1 1 d . . . . .
O2 O 0.43478(11) 0.18877(11) 0.71971(11) 0.0648(4) Uani 1 1 d . . . . .
O1 O -0.00020(14) 0.56257(12) 0.34168(12) 0.0748(4) Uani 1 1 d . . . . .
C11 C 0.31326(15) 0.27692(14) 0.52587(15) 0.0573(4) Uani 1 1 d . . . . .
C10 C 0.22755(16) 0.32218(15) 0.56085(15) 0.0593(4) Uani 1 1 d . . . . .
H10 H 0.232232 0.308436 0.635898 0.071 Uiso 1 1 calc R U . . .
C13 C 0.21034(15) 0.36039(16) 0.34032(15) 0.0600(4) Uani 1 1 d . . . . .
H13 H 0.203754 0.371999 0.264364 0.072 Uiso 1 1 calc R U . . .
C12 C 0.30316(15) 0.29788(15) 0.41455(15) 0.0597(4) Uani 1 1 d . . . . .
H12 H 0.360794 0.268858 0.389312 0.072 Uiso 1 1 calc R U . . .
C4 C -0.08947(16) 0.53769(16) 0.10347(16) 0.0625(4) Uani 1 1 d . . . . .
H4 H -0.087694 0.612785 0.130283 0.075 Uiso 1 1 calc R U . . .
C8 C 0.12694(15) 0.40608(15) 0.37680(15) 0.0575(4) Uani 1 1 d . . . . .
C9 C 0.13621(16) 0.38660(16) 0.48780(16) 0.0602(4) Uani 1 1 d . . . . .
H9 H 0.079657 0.417627 0.513378 0.072 Uiso 1 1 calc R U . . .
C7 C 0.02914(16) 0.47990(16) 0.30186(16) 0.0614(4) Uani 1 1 d . . . . .
C5 C -0.03154(15) 0.45137(16) 0.17921(15) 0.0596(4) Uani 1 1 d . . . . .
C3 C -0.14911(16) 0.51369(18) -0.01011(17) 0.0669(5) Uani 1 1 d . . . . .
H3 H -0.187159 0.572585 -0.061639 0.080 Uiso 1 1 calc R U . . .
C6 C -0.03713(16) 0.34112(16) 0.13932(17) 0.0640(5) Uani 1 1 d . . . . .
H6 H 0.001503 0.282002 0.190283 0.077 Uiso 1 1 calc R U . . .
C15 C 0.59397(17) 0.11705(18) 0.68096(17) 0.0671(5) Uani 1 1 d . . . . .
C1 C -0.09876(17) 0.31767(18) 0.02579(18) 0.0694(5) Uani 1 1 d . . . . .
H1 H -0.103523 0.242219 -0.000923 0.083 Uiso 1 1 calc R U . . .
C2 C -0.15371(17) 0.40387(19) -0.04931(18) 0.0702(5) Uani 1 1 d . . . . .
H2 H -0.194513 0.387708 -0.127648 0.084 Uiso 1 1 calc R U . . .
C19 C 0.6425(2) 0.0083(2) 0.6536(2) 0.0872(7) Uani 1 1 d . . . . .
H19A H 0.579415 -0.047624 0.624877 0.131 Uiso 1 1 calc R U . . .
H19B H 0.704414 -0.020730 0.722510 0.131 Uiso 1 1 calc R U . . .
H19C H 0.674917 0.022986 0.595748 0.131 Uiso 1 1 calc R U . . .
C18 C 0.68845(19) 0.2074(2) 0.7153(2) 0.0824(6) Uani 1 1 d . . . . .
H18A H 0.714693 0.220468 0.652839 0.124 Uiso 1 1 calc R U . . .
H18B H 0.755002 0.182320 0.782694 0.124 Uiso 1 1 calc R U . . .
H18C H 0.656647 0.277584 0.732589 0.124 Uiso 1 1 calc R U . . .
C16 C 0.4690(2) -0.0077(2) 0.7554(3) 0.0898(7) Uani 1 1 d . . . . .
H16A H 0.419185 -0.005656 0.799657 0.135 Uiso 1 1 calc R U . . .
H16B H 0.528188 -0.067092 0.785291 0.135 Uiso 1 1 calc R U . . .
H16C H 0.420531 -0.023624 0.675720 0.135 Uiso 1 1 calc R U . . .
B1 B 0.41803(18) 0.20673(17) 0.60872(18) 0.0591(5) Uani 1 1 d . . . . .
C17 C 0.6032(2) 0.1338(2) 0.88655(18) 0.0838(7) Uani 1 1 d . . . . .
H17A H 0.629338 0.212495 0.891553 0.126 Uiso 1 1 calc R U . . .
H17B H 0.671624 0.083872 0.914241 0.126 Uiso 1 1 calc R U . . .
H17C H 0.556448 0.123642 0.933082 0.126 Uiso 1 1 calc R U . . .
C14 C 0.52916(17) 0.10528(17) 0.76417(17) 0.0667(5) 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
O3 C15 1.463(2) . ?
O3 B1 1.356(3) . ?
O2 B1 1.366(2) . ?
O2 C14 1.466(2) . ?
O1 C7 1.220(2) . ?
C11 C10 1.402(3) . ?
C11 C12 1.398(3) . ?
C11 B1 1.560(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(3) . ?
C13 C8 1.391(3) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.400(3) . ?
C4 C3 1.380(3) . ?
C8 C9 1.394(3) . ?
C8 C7 1.501(2) . ?
C9 H9 0.9500 . ?
C7 C5 1.491(3) . ?
C5 C6 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.381(3) . ?
C15 C19 1.516(3) . ?
C15 C18 1.518(3) . ?
C15 C14 1.560(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C2 H2 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C14 1.514(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C14 1.514(3) . ?

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
B1 O3 C15 107.36(15) . . ?
B1 O2 C14 106.76(14) . . ?
C10 C11 B1 121.29(16) . . ?
C12 C11 C10 118.01(16) . . ?
C12 C11 B1 120.70(16) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 121.07(17) . . ?
C9 C10 H10 119.5 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C8 120.20(17) . . ?
C8 C13 H13 119.9 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.09(17) . . ?
C13 C12 H12 119.5 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.99(18) . . ?
C13 C8 C9 119.40(16) . . ?
C13 C8 C7 122.13(16) . . ?
C9 C8 C7 118.43(16) . . ?
C10 C9 C8 120.22(17) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
O1 C7 C8 119.82(17) . . ?
O1 C7 C5 120.55(17) . . ?
C5 C7 C8 119.63(15) . . ?
C4 C5 C7 118.46(17) . . ?
C6 C5 C4 119.46(17) . . ?
C6 C5 C7 122.00(16) . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.22(18) . . ?
C2 C3 H3 119.9 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.09(18) . . ?
C1 C6 H6 120.0 . . ?
O3 C15 C19 108.82(16) . . ?
O3 C15 C18 105.86(17) . . ?
O3 C15 C14 102.28(14) . . ?
C19 C15 C18 109.74(19) . . ?
C19 C15 C14 115.5(2) . . ?
C18 C15 C14 113.82(18) . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.21(19) . . ?
C2 C1 H1 119.9 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.01(19) . . ?
C1 C2 H2 120.0 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
O3 B1 O2 113.92(16) . . ?
O3 B1 C11 123.26(18) . . ?
O2 B1 C11 122.82(17) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
O2 C14 C15 102.42(15) . . ?
O2 C14 C16 105.83(16) . . ?
O2 C14 C17 108.93(16) . . ?
C16 C14 C15 113.19(19) . . ?
C17 C14 C15 114.61(17) . . ?
C17 C14 C16 111.0(2) . . ?

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 C15 C14 O2 -26.36(18) . . . . ?
O3 C15 C14 C16 87.11(18) . . . . ?
O3 C15 C14 C17 -144.15(18) . . . . ?
O1 C7 C5 C4 23.2(3) . . . . ?
O1 C7 C5 C6 -153.5(2) . . . . ?
C11 C10 C9 C8 1.0(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 B1 O3 178.08(17) . . . . ?
C10 C11 B1 O2 -2.4(3) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C13 C8 C7 O1 -139.9(2) . . . . ?
C13 C8 C7 C5 40.2(3) . . . . ?
C12 C11 C10 C9 -0.6(3) . . . . ?
C12 C11 B1 O3 -2.9(3) . . . . ?
C12 C11 B1 O2 176.67(17) . . . . ?
C12 C13 C8 C9 -1.3(3) . . . . ?
C12 C13 C8 C7 176.30(16) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C8 C13 C12 C11 1.7(3) . . . . ?
C8 C7 C5 C4 -156.92(17) . . . . ?
C8 C7 C5 C6 26.4(3) . . . . ?
C9 C8 C7 O1 37.7(3) . . . . ?
C9 C8 C7 C5 -142.24(18) . . . . ?
C7 C8 C9 C10 -177.77(16) . . . . ?
C7 C5 C6 C1 177.07(18) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C5 C6 C1 C2 1.1(3) . . . . ?
C3 C4 C5 C7 -178.29(17) . . . . ?
C3 C4 C5 C6 -1.5(3) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C15 O3 B1 O2 -8.9(2) . . . . ?
C15 O3 B1 C11 170.68(17) . . . . ?
C19 C15 C14 O2 -144.38(17) . . . . ?
C19 C15 C14 C16 -30.9(2) . . . . ?
C19 C15 C14 C17 97.8(2) . . . . ?
C18 C15 C14 O2 87.33(18) . . . . ?
C18 C15 C14 C16 -159.20(18) . . . . ?
C18 C15 C14 C17 -30.5(2) . . . . ?
B1 O3 C15 C19 144.5(2) . . . . ?
B1 O3 C15 C18 -97.60(19) . . . . ?
B1 O3 C15 C14 21.84(19) . . . . ?
B1 O2 C14 C15 22.10(18) . . . . ?
B1 O2 C14 C16 -96.7(2) . . . . ?
B1 O2 C14 C17 143.87(19) . . . . ?
B1 C11 C10 C9 178.50(16) . . . . ?
B1 C11 C12 C13 -179.90(16) . . . . ?
C14 O2 B1 O3 -9.4(2) . . . . ?
C14 O2 B1 C11 170.99(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
