# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_BP(OH)2DCEt2
_database_code_depnum_ccdc_archive 'CCDC 2004784'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2020-05-19 deposited with the CCDC.	2021-01-06 downloaded from the CCDC.
;
# 22278GuillotICMMO
# Yu2165 LCI   



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H16 N2 O6'
_chemical_formula_sum            'C16 H16 N2 O6'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         332.31

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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3814(6)
_cell_length_b                   11.6206(5)
_cell_length_c                   8.1169(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.453(2)
_cell_angle_gamma                90
_cell_volume                     1508.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.57
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8779
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15738
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.166
_diffrn_reflns_theta_max         30.642
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2310
_reflns_number_gt                1743
_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.
 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0621P)²+0.9885P] 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         2310
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.89294(8) 0.53292(12) 0.60817(18) 0.0291(3) Uani 1 1 d . . . . .
H1A H 0.9113 0.4845 0.7049 0.044 Uiso 1 1 calc R U . . .
H1B H 0.9404 0.5576 0.5656 0.044 Uiso 1 1 calc R U . . .
H1C H 0.8554 0.4906 0.5222 0.044 Uiso 1 1 calc R U . . .
C2 C 0.84871(8) 0.63608(11) 0.65775(16) 0.0250(3) Uani 1 1 d . . . . .
H2A H 0.8864 0.6806 0.7428 0.030 Uiso 1 1 calc R U . . .
H2B H 0.8287 0.6849 0.5605 0.030 Uiso 1 1 calc R U . . .
C3 C 0.72987(7) 0.67307(11) 0.77188(14) 0.0216(2) Uani 1 1 d . . . . .
C4 C 0.66148(7) 0.62095(10) 0.84181(14) 0.0202(2) Uani 1 1 d . . . . .
C5 C 0.60703(8) 0.69375(10) 0.89977(15) 0.0224(2) Uani 1 1 d . . . . .
H5 H 0.6138 0.7730 0.8949 0.027 Uiso 1 1 calc R U . . .
C6 C 0.54241(7) 0.64856(10) 0.96506(14) 0.0200(2) Uani 1 1 d . . . . .
C7 C 0.53367(7) 0.52794(9) 0.96798(13) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.65020(7) 0.50234(10) 0.84994(14) 0.0197(2) Uani 1 1 d . . . . .
H8 H 0.6870 0.4531 0.8121 0.024 Uiso 1 1 calc R U . . .
N1 N 0.58767(6) 0.45804(9) 0.91090(12) 0.0194(2) Uani 1 1 d . . . . .
O1 O 0.77887(5) 0.59358(8) 0.72450(11) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.73953(6) 0.77566(8) 0.76036(13) 0.0311(2) Uani 1 1 d . . . . .
O3 O 0.49123(6) 0.72160(8) 1.02416(12) 0.0275(2) Uani 1 1 d . . . . .
H3 H 0.4539 0.6850 1.0530 0.041 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0253(6) 0.0336(7) 0.0304(6) -0.0060(5) 0.0103(5) -0.0040(5)
C2 0.0224(6) 0.0295(6) 0.0251(6) 0.0004(5) 0.0096(5) -0.0045(5)
C3 0.0202(5) 0.0257(6) 0.0185(5) 0.0012(4) 0.0030(4) -0.0008(4)
C4 0.0192(5) 0.0241(6) 0.0168(5) 0.0005(4) 0.0026(4) -0.0014(4)
C5 0.0242(6) 0.0199(5) 0.0225(5) 0.0003(4) 0.0041(4) -0.0003(4)
C6 0.0210(5) 0.0196(5) 0.0190(5) -0.0009(4) 0.0037(4) 0.0014(4)
C7 0.0180(5) 0.0196(5) 0.0138(5) -0.0012(4) 0.0022(4) 0.0007(4)
C8 0.0192(5) 0.0230(5) 0.0171(5) -0.0015(4) 0.0044(4) 0.0013(4)
N1 0.0200(5) 0.0211(5) 0.0171(4) -0.0013(4) 0.0038(4) 0.0009(4)
O1 0.0216(4) 0.0255(5) 0.0255(4) 0.0002(3) 0.0091(3) -0.0023(3)
O2 0.0316(5) 0.0245(5) 0.0405(5) 0.0035(4) 0.0149(4) -0.0020(4)
O3 0.0282(5) 0.0217(4) 0.0362(5) -0.0031(4) 0.0152(4) 0.0005(3)

_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 1.5000(19) . ?
C2 O1 1.4539(14) . ?
C3 O2 1.2088(16) . ?
C3 O1 1.3337(15) . ?
C3 C4 1.4895(16) . ?
C4 C5 1.3834(17) . ?
C4 C8 1.3941(17) . ?
C5 C6 1.3853(17) . ?
C6 O3 1.3516(14) . ?
C6 C7 1.4097(16) . ?
C7 N1 1.3541(15) . ?
C7 C7 1.468(2) 5_667 ?
C8 N1 1.3333(15) . ?

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
O1 C2 C1 107.03(10) . . ?
O2 C3 O1 124.32(11) . . ?
O2 C3 C4 123.53(12) . . ?
O1 C3 C4 112.16(10) . . ?
C5 C4 C8 119.13(11) . . ?
C5 C4 C3 118.30(11) . . ?
C8 C4 C3 122.57(11) . . ?
C4 C5 C6 120.01(11) . . ?
O3 C6 C5 118.77(10) . . ?
O3 C6 C7 123.06(11) . . ?
C5 C6 C7 118.17(11) . . ?
N1 C7 C6 120.96(10) . . ?
N1 C7 C7 116.87(12) . 5_667 ?
C6 C7 C7 122.17(13) . 5_667 ?
N1 C8 C4 121.31(11) . . ?
C8 N1 C7 120.41(10) . . ?
C3 O1 C2 116.30(10) . . ?

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL 2278_0m in C2/c
CELL  0.71073  16.3814  11.6206   8.1169   90.000  102.453   90.000
ZERR     4.00   0.0006   0.0005   0.0003    0.000    0.002    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  64   64   8    24
MERG   2
FMAP   2
PLAN   20
SIZE     0.080   0.090   0.210
ACTA    50.00
BOND
WPDB  -2
L.S.  20
TEMP    20.00
WGHT    0.062100    0.988500
FVAR       0.06739
MOLE    1
C1    1    0.892942    0.532918    0.608174    11.00000    0.02530    0.03363 =
         0.03040   -0.00602    0.01029   -0.00396
AFIX 137
H1A   2    0.911339    0.484527    0.704917    11.00000   -1.50000
H1B   2    0.940403    0.557587    0.565642    11.00000   -1.50000
H1C   2    0.855392    0.490613    0.522234    11.00000   -1.50000
AFIX   0
C2    1    0.848711    0.636084    0.657750    11.00000    0.02240    0.02954 =
         0.02506    0.00039    0.00959   -0.00450
AFIX  23
H2A   2    0.886380    0.680609    0.742750    11.00000   -1.20000
H2B   2    0.828708    0.684910    0.560496    11.00000   -1.20000
AFIX   0
C3    1    0.729871    0.673075    0.771881    11.00000    0.02017    0.02568 =
         0.01846    0.00120    0.00295   -0.00080
C4    1    0.661477    0.620946    0.841814    11.00000    0.01918    0.02410 =
         0.01680    0.00049    0.00256   -0.00140
C5    1    0.607027    0.693750    0.899775    11.00000    0.02424    0.01990 =
         0.02254    0.00033    0.00406   -0.00030
AFIX  43
H5    2    0.613804    0.773047    0.894911    11.00000   -1.20000
AFIX   0
C6    1    0.542409    0.648558    0.965061    11.00000    0.02100    0.01962 =
         0.01899   -0.00087    0.00375    0.00135
C7    1    0.533668    0.527937    0.967975    11.00000    0.01798    0.01959 =
         0.01378   -0.00119    0.00219    0.00070
C8    1    0.650197    0.502340    0.849942    11.00000    0.01922    0.02297 =
         0.01712   -0.00148    0.00438    0.00129
AFIX  43
H8    2    0.687015    0.453144    0.812093    11.00000   -1.20000
AFIX   0
N1    3    0.587667    0.458037    0.910905    11.00000    0.02003    0.02108 =
         0.01714   -0.00128    0.00383    0.00087
O1    4    0.778873    0.593583    0.724505    11.00000    0.02155    0.02550 =
         0.02553    0.00023    0.00911   -0.00226
O2    4    0.739532    0.775658    0.760357    11.00000    0.03157    0.02452 =
         0.04054    0.00346    0.01485   -0.00195
O3    4    0.491232    0.721601    1.024155    11.00000    0.02816    0.02175 =
         0.03625   -0.00309    0.01520    0.00053
AFIX 147
H3    2    0.453877    0.684953    1.052995    11.00000   -1.50000
AFIX   0
HKLF    4

REM  2278_0m in C2/c
REM R1 =  0.0415 for    1743 Fo > 4sig(Fo)  and  0.0597 for all    2310 data
REM    111 parameters refined using      0 restraints

END

WGHT      0.0621      0.9877

REM Highest difference peak  0.511,  deepest hole -0.251,  1-sigma level  0.052
Q1    1   0.4125  0.6704  1.0658  11.00000  0.05    0.51
Q2    1   0.5387  0.5882  0.9709  11.00000  0.05    0.44
Q3    1   0.6581  0.5636  0.8542  11.00000  0.05    0.40
Q4    1   0.5757  0.6669  0.9423  11.00000  0.05    0.33
Q5    1   0.5000  0.5000  1.0000  10.50000  0.05    0.32
Q6    1   0.6961  0.6463  0.8190  11.00000  0.05    0.30
Q7    1   0.6356  0.6538  0.8742  11.00000  0.05    0.27
Q8    1   0.5822  0.4005  0.9093  11.00000  0.05    0.26
Q9    1   0.7686  0.5359  0.7311  11.00000  0.05    0.25
Q10   1   0.5603  0.4969  0.9377  11.00000  0.05    0.23
Q11   1   0.7192  0.7256  0.7358  11.00000  0.05    0.23
Q12   1   0.8813  0.5945  0.6386  11.00000  0.05    0.21
Q13   1   0.6077  0.7228  0.8967  11.00000  0.05    0.21
Q14   1   0.7062  0.4187  0.7942  11.00000  0.05    0.21
Q15   1   0.6149  0.4836  0.8761  11.00000  0.05    0.19
Q16   1   0.8502  0.7185  0.6434  11.00000  0.05    0.18
Q17   1   0.7610  0.6388  0.7278  11.00000  0.05    0.17
Q18   1   0.8871  0.4589  0.6160  11.00000  0.05    0.15
Q19   1   0.8169  0.6201  0.6880  11.00000  0.05    0.15
Q20   1   0.8191  0.7193  0.5936  11.00000  0.05    0.13
;
_shelx_res_checksum              13899
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration .

